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What's the right thing to do in this situation?

Say I have two liabilities: - a tax bill, which will be due at the end of the year. - a mortgage, which is due over the course of many (> 5) years. I have enough money to pay off both the tax bill and the mortgage immediately if I wanted, but if possible, I'd like to invest the funds instead for hig...
by johnanglemen
Tue Apr 23, 2013 7:36 pm
 
Forum: Investing - Help with Personal Investments
Topic: What's the right thing to do in this situation?
Replies: 5
Views: 941

Paying taxes past your credit limit

The IRS offers a payment provider, PayUSAtax.com, that charges 1.89% to process CC tax payments. There are a number of cards that pay larger rewards than this. If you have a tax payment that is much larger than your CC limit, does anyone know if it's possible to break it up into multiple payments? I...
by johnanglemen
Mon Apr 08, 2013 8:15 pm
 
Forum: Personal Finance (Not Investing)
Topic: Paying taxes past your credit limit
Replies: 12
Views: 873

What denominator is used to calculate dividend yield?

I invest $10,000 in Total Stock Market on January 1. By December 31, it has thankfully appreciated to $20,000. The fund typically yields an annual dividend of 2%. Should I be expecting 2% of $10K, $20K, or something in between depending on the fund's value throughout the year?
by johnanglemen
Sun Apr 07, 2013 7:22 pm
 
Forum: Investing - Help with Personal Investments
Topic: What denominator is used to calculate dividend yield?
Replies: 3
Views: 303

How to determine what % of a Q1 dividend was qualified?

OK, so a bunch of funds just paid out dividends for Q1. Now how do I tell what % of these specific dividends were qualified (not the fund's general average)? I thought this would be rather simple information to obtain, but I can't find it anywhere.
by johnanglemen
Fri Apr 05, 2013 2:54 am
 
Forum: Investing - Help with Personal Investments
Topic: How to determine what % of a Q1 dividend was qualified?
Replies: 2
Views: 198

Re: First time tax loss harvest questions

Thanks. Not an April Fools joke. I thought about adding to my tax-managed international position in the interim, but it seems somewhat illogical because the fund isn't really correlated with emerging markets (e.g. YTD, VEMIX is +4% while VWO is -3.7%). Why exactly wouldn't you just go to IEMG? Is it...
by johnanglemen
Mon Apr 01, 2013 12:41 pm
 
Forum: Investing - Theory, News & General
Topic: First time tax loss harvest questions
Replies: 7
Views: 596

First time tax loss harvest questions

I have a loss of $130K in Vanguard Emerging Markets Institutional (VEMIX) that represents a 2.5% decline. I am considering harvesting this loss and purchasing iShares Core MSCI Emerging Markets ETF (IEMG) as a substitute to remain in the market. A few questions: 1. Does it make sense to harvest this...
by johnanglemen
Mon Apr 01, 2013 2:45 am
 
Forum: Investing - Theory, News & General
Topic: First time tax loss harvest questions
Replies: 7
Views: 596

Best wash sale replacement for Vanguard Emerging Markets?

Does anyone know of a suitable low-cost wash-sale replacement for Vanguard Emerging Markets Admiral fund? I prefer a mutual fund but would settle for an ETF. The lowest cost option that tracks a different index seems to be iShares Emerging Markets (IEMG). Would others agree with that? Is the bid/ask...
by johnanglemen
Mon Apr 01, 2013 12:17 am
 
Forum: Investing - Help with Personal Investments
Topic: Best wash sale replacement for Vanguard Emerging Markets?
Replies: 1
Views: 295

Re: Why doesn't this fund have an SEC Yield?

Can someone help me understand why this fund has neither an SEC Yield nor a Distribution Yield listed? https://personal.vanguard.com/us/funds/snapshot?FundId=0127&FundIntExt=INT#tab=4 Did you read through the Wiki? Link - http://www.bogleheads.org/wiki/Vanguard_Tax_Managed_International_Fund_Ta...
by johnanglemen
Tue Mar 26, 2013 1:55 pm
 
Forum: Investing - Help with Personal Investments
Topic: Why doesn't this fund have an SEC Yield?
Replies: 10
Views: 656

Why doesn't this fund have an SEC Yield?

Can someone help me understand why this fund has neither an SEC Yield nor a Distribution Yield listed?

https://personal.vanguard.com/us/funds/ ... =INT#tab=4
by johnanglemen
Tue Mar 26, 2013 4:39 am
 
Forum: Investing - Help with Personal Investments
Topic: Why doesn't this fund have an SEC Yield?
Replies: 10
Views: 656

Re: How do you TLH state munis?

OP, 2 thoughts. 1. You appear to be down about 1.2% on the investment. Looking at muni funds in general, they had been on a continuous rise for a few years until a few months ago and are now down less than 2% from their high. This concerns me as it suggests that you bought almost all of the 5 MM in...
by johnanglemen
Tue Mar 12, 2013 3:51 pm
 
Forum: Investing - Help with Personal Investments
Topic: How do you TLH state munis?
Replies: 15
Views: 604

Re: How do you TLH state munis?

I have $5M in Munis and around $60K in losses. Is that not worth harvesting?
by johnanglemen
Mon Mar 11, 2013 12:12 pm
 
Forum: Investing - Help with Personal Investments
Topic: How do you TLH state munis?
Replies: 15
Views: 604

How do you TLH state munis?

I hold Vanguard California Intermediate Tax-Exempt (VCADX). How would people recommend tax-loss harvesting this? Would I just switch to the national muni (VWIUX)? My California income tax rate is 13.3% so I presumably would not want to hold the national munis for any longer than I need to. Is it cra...
by johnanglemen
Mon Mar 11, 2013 11:27 am
 
Forum: Investing - Help with Personal Investments
Topic: How do you TLH state munis?
Replies: 15
Views: 604

Re: How do you estimate dividends for tax purposes?

And is there a good site for looking up these historical dividend yields expressed as percentages per year, rather than in raw dollar amounts per quarter? (I see the Bogleheads wiki does that for some funds, but not all of them).
by johnanglemen
Mon Mar 11, 2013 4:48 am
 
Forum: Investing - Help with Personal Investments
Topic: How do you estimate dividends for tax purposes?
Replies: 7
Views: 454

How do you estimate dividends for tax purposes?

In order to file my quarterly estimated taxes, my CPA recommends projecting my income out for the year. Nothing is perfect, but what's the best means of estimating a fund's dividends? Is it just averaging up its historical dividends? Also, are December distributions typically larger than any other q...
by johnanglemen
Mon Mar 11, 2013 4:43 am
 
Forum: Investing - Help with Personal Investments
Topic: How do you estimate dividends for tax purposes?
Replies: 7
Views: 454

Re: Are long-term bonds the best if you're sure you'll hold

If you know with absolute certainty that you'll hold a long-term bond fund for at least its average duration, if not much longer, should you buy long-term muni bonds rather than intermediate-term muni bonds? This board always seems to recommend intermediate, but I'm curious why if you can guarantee...
by johnanglemen
Thu Mar 07, 2013 7:36 am
 
Forum: Investing - Theory, News & General
Topic: Are long-term bonds the best if you're sure you'll hold them
Replies: 8
Views: 902

Are long-term bonds the best if you're sure you'll hold them

If you know with absolute certainty that you'll hold a long-term bond fund for at least its average duration, if not much longer, should you buy long-term muni bonds rather than intermediate-term muni bonds? This board always seems to recommend intermediate, but I'm curious why if you can guarantee ...
by johnanglemen
Thu Feb 28, 2013 8:23 pm
 
Forum: Investing - Theory, News & General
Topic: Are long-term bonds the best if you're sure you'll hold them
Replies: 8
Views: 902

Re: Tax-managed fund recommendations given new tax laws

Could you update this post now that the ER for Total International has dropped?
by johnanglemen
Thu Feb 28, 2013 8:35 am
 
Forum: Investing - Theory, News & General
Topic: Tax-managed fund recommendations given new tax laws
Replies: 10
Views: 2001

Vanguard lowers expense ratios for VEU and VSS!

As of 2/28/2013:

VEU (Vanguard FTSE All-World ex-US ETF) changes from 0.18% to 0.15%
VSS (Vanguard FTSE All-World ex-US Small-Cap ETF) changes from 0.28% to 0.25%
by johnanglemen
Thu Feb 28, 2013 5:31 am
 
Forum: Investing - Theory, News & General
Topic: Vanguard lowers expense ratios for VEU and VSS!
Replies: 3
Views: 890

Re: What's the difference between tax-managed funds & adviso

Vanguard's tax-managed funds do not attempt to outperform their index. Active managers do attempt to outperform their index. Pretty clear, no? No. Tax-managed funds do attempt to outperform benchmarks in terms of net return. That's why you use them over "tax unmanaged" funds in the first ...
by johnanglemen
Sat Jan 19, 2013 1:22 am
 
Forum: Investing - Theory, News & General
Topic: What's the difference between tax-managed funds & advisors?
Replies: 9
Views: 527

Re: What's the difference between tax-managed funds & adviso

I get the technical difference. I was really asking what's different in terms of this board's philosophy. People here instinctively shoot down the idea of an advisor (and admittedly I'm one of them), but all kinds of active management optimization tricks -- such as tax-managed funds, or small cap ti...
by johnanglemen
Fri Jan 18, 2013 9:06 pm
 
Forum: Investing - Theory, News & General
Topic: What's the difference between tax-managed funds & advisors?
Replies: 9
Views: 527

What's the difference between tax-managed funds & advisors?

A tax-managed fund is actively managed to optimize your return. An advisor actively manages to optimize your return. Not all advisors just put you in expensive funds; some claim they'll do low-cost passive indexing, but better (e.g. by managing for taxes). So what's the difference?
by johnanglemen
Fri Jan 18, 2013 3:17 pm
 
Forum: Investing - Theory, News & General
Topic: What's the difference between tax-managed funds & advisors?
Replies: 9
Views: 527

Re: Tax-managed funds are now more attractive

Would love to understand whether the situation has changed at all with the resolution of the fiscal cliff, as xram said earlier. Also, grabiner, how do you personally make a long-term decision here? For instance, three-fund international happens to beat total international today, but couldn't a tiny...
by johnanglemen
Fri Jan 18, 2013 2:14 pm
 
Forum: Investing - Theory, News & General
Topic: Tax-managed funds are now more attractive
Replies: 18
Views: 3972

Re: Tax-managed funds are now more attractive

TM International versus Total International ... You might also have your own capital gains rebalancing the three-fund combination, and it is definitely more complicated to manage. Thus, it doesn't have a clear advantage if you want to hold international stocks at the market weight. However, if you ...
by johnanglemen
Mon Jan 14, 2013 3:17 pm
 
Forum: Investing - Theory, News & General
Topic: Tax-managed funds are now more attractive
Replies: 18
Views: 3972

Re: What's the optimal way to live off windfalls or savings?

Given the knowledge that you'll need to withdraw $X per year, there must obviously be some difference between investing $X in equity for as long as possible and then selling it off as required versus keeping $X in cash. The former seems to have greater expected return but also the greatest risk, so...
by johnanglemen
Fri Jan 11, 2013 11:39 am
 
Forum: Investing - Theory, News & General
Topic: What's the optimal way to live off windfalls or savings?
Replies: 26
Views: 2046

Re: Would this provide greater returns over the long run?

Two answers: Of course the overall return of your investments would be increased if you increase your exposure to risk and return, on average. This return can be dragged down by tax and transaction costs, however, or even by inefficiency in being in zero return transitional cash rather than interes...
by johnanglemen
Fri Jan 11, 2013 11:29 am
 
Forum: Investing - Theory, News & General
Topic: Would this provide greater returns over the long run?
Replies: 43
Views: 2136

Re: What's the optimal way to live off windfalls or savings?

I'd research the scores of posts on this forum concerning (a) income funds, (b) dividend investing, and (c) investing for "total return" including dividends, fixed income and growth. You need to understand c) to answer this question. Short answer: There is no relationship at all between &...
by johnanglemen
Fri Jan 11, 2013 11:22 am
 
Forum: Investing - Theory, News & General
Topic: What's the optimal way to live off windfalls or savings?
Replies: 26
Views: 2046

Re: Would this provide greater returns over the long run?

Reviving this old theoretical question. It seems the consensus in this thread was that the scenario posed would in fact lead to greater expected returns over the long run. However, I've been reading about the sequence of returns risk and I'm having trouble reconciling that concept with this consensu...
by johnanglemen
Fri Jan 11, 2013 10:56 am
 
Forum: Investing - Theory, News & General
Topic: Would this provide greater returns over the long run?
Replies: 43
Views: 2136

Re: What's the optimal way to live off windfalls or savings?

I am curious why the answer isn't something like "figure out a good AA given your age and outlook, as always, and then just sell some additional shares each year to cover the gap between the dividends and the necessary funds." Could somebody clarify? That's what I do, but I would add &quo...
by johnanglemen
Fri Jan 11, 2013 9:46 am
 
Forum: Investing - Theory, News & General
Topic: What's the optimal way to live off windfalls or savings?
Replies: 26
Views: 2046

Re: What's the optimal way to live off windfalls or savings?

Your job pays $50K aftertax per year but you need $80K a year to live. What would you do there? I would say you're spending too much> :oops: Bruce I wouldn't say so. Let's say that you actually do earn just about 80K a year, but most of that money isn't coming in *per paycheck* when you need it. Fo...
by johnanglemen
Fri Jan 11, 2013 9:42 am
 
Forum: Investing - Theory, News & General
Topic: What's the optimal way to live off windfalls or savings?
Replies: 26
Views: 2046

Re: What's the optimal way to live off windfalls or savings?

(a) Increase your bond allocation so that you generate enough fixed income to live off of? This seems wrong since it changes your asset allocation . Your circumstances have changed radically so there is no reason that an AA established before the change must remain the same. You can buy an annuity ...
by johnanglemen
Fri Jan 11, 2013 9:39 am
 
Forum: Investing - Theory, News & General
Topic: What's the optimal way to live off windfalls or savings?
Replies: 26
Views: 2046

Re: What's the optimal way to live off windfalls or savings?

70% TSM, 30% TISM, just live off the dividends. What if the dividends aren't enough and you need some of the principal, too? For instance, you get a big windfall of $1M. Your job pays $50K aftertax per year but you need $80K a year to live. What would you do there? Is it better to leave money in ca...
by johnanglemen
Fri Jan 11, 2013 3:47 am
 
Forum: Investing - Theory, News & General
Topic: What's the optimal way to live off windfalls or savings?
Replies: 26
Views: 2046

Re: What's the optimal way to live off windfalls or savings?

I've been reading the forum since 2009 so that's not very helpful.... can you be more specific? Investing in dividend funds seems to have the same issue as investing in additional bond funds in terms of unnaturally mucking with your asset allocation and your risk/reward simply to avoid incurring any...
by johnanglemen
Fri Jan 11, 2013 2:45 am
 
Forum: Investing - Theory, News & General
Topic: What's the optimal way to live off windfalls or savings?
Replies: 26
Views: 2046

What's the optimal way to live off windfalls or savings?

Let's say you've gotten a windfall or you've otherwise built up a large savings, and you need to supplement your regular income stream with money from that large lump. Let's also assume that income from your bond holdings is not large enough to fully cover these expenses. Lastly, assume that the win...
by johnanglemen
Fri Jan 11, 2013 2:25 am
 
Forum: Investing - Theory, News & General
Topic: What's the optimal way to live off windfalls or savings?
Replies: 26
Views: 2046

Re: 6-month rule for tax loss harvesting muni bonds

That would be true of bond funds that don't accrue interest daily. Vanguard muni funds do (not don't), at least all that I know about, as do the taxable bond funds, with one notable exception. I didn't follow that. Can you clarify? What is different about Vanguard muni funds relative to my question?
by johnanglemen
Sun Jan 06, 2013 2:19 pm
 
Forum: Investing - Help with Personal Investments
Topic: 6-month rule for tax loss harvesting muni bonds
Replies: 4
Views: 192

6-month rule for tax loss harvesting muni bonds

I realize that you have to deduct the value of dividends received when tax-loss harvesting a tax-exempt muni bond fund purchased within 6 months. However, this is only for dividends received up until the day you sell, right? Not based on future dividends received within the 6 month window, or anythi...
by johnanglemen
Sun Jan 06, 2013 2:15 pm
 
Forum: Investing - Help with Personal Investments
Topic: 6-month rule for tax loss harvesting muni bonds
Replies: 4
Views: 192

Re: Is there any benefit to tax loss harvesting in this case

It seems like I haven't actually gained anything in this case. I've offset my short term gain in the new fund with the long term loss in the old fund. If that's true, does that mean that people generally hold onto the replacement fund for the long haul rather than selling it after 31 days? You did ...
by johnanglemen
Sun Jan 06, 2013 2:03 pm
 
Forum: Investing - Help with Personal Investments
Topic: Is there any benefit to tax loss harvesting in this case?
Replies: 8
Views: 320

Re: Is there any benefit to tax loss harvesting in this case

Just to be clear, my assumption is that I have multiple cost bases in a fund and only some of them are at a loss. So I wouldn't be liquidating the entire fund. Instead, I'd end up holding two funds for each asset of my portfolio forever, the "original" and the TLH alternative.
by johnanglemen
Sun Jan 06, 2013 1:40 pm
 
Forum: Investing - Help with Personal Investments
Topic: Is there any benefit to tax loss harvesting in this case?
Replies: 8
Views: 320

Re: Is there any benefit to tax loss harvesting in this case

Yeah, maybe not "years ago", just a year ago. I just meant to suggest that it was a long-term loss although I guess it doesn't even matter.

It's good to understand that people hold their replacement shares forever. Is that a general rule of thumb?
by johnanglemen
Sun Jan 06, 2013 1:39 pm
 
Forum: Investing - Help with Personal Investments
Topic: Is there any benefit to tax loss harvesting in this case?
Replies: 8
Views: 320

Is there any benefit to tax loss harvesting in this case?

A fund that I bought years ago drops 3%. I TLH by selling it and immediately buying a very similar (not identical) fund. I hold the similar fund for 31 days. During that period, the asset bounces back up to its prior level, erasing the 3% loss. I simplify my portfolio by selling the similar fund and...
by johnanglemen
Sun Jan 06, 2013 1:34 pm
 
Forum: Investing - Help with Personal Investments
Topic: Is there any benefit to tax loss harvesting in this case?
Replies: 8
Views: 320

Forecasting practical return from muni bond

I'm living off fixed income from a Vanguard muni bond fund. When forecasting how much I should expect to earn from the dividends of these bonds in the future, should I be using the distribution yield or the SEC yield? My understanding is that I should be using the SEC yield, which is currently aroun...
by johnanglemen
Wed Jan 02, 2013 2:40 am
 
Forum: Investing - Help with Personal Investments
Topic: Forecasting practical return from muni bond
Replies: 4
Views: 317

Re: Still a bit confused about wash sales

One needs to understand the concept of replacement shares. That is, one has to still own shares that replaced the shares you sold at a loss. If you buy and sell the same shares, there are no replacement shares unless you have bought more shares either before or after the shares you wrote about. Now...
by johnanglemen
Sat Dec 29, 2012 2:30 am
 
Forum: Investing - Help with Personal Investments
Topic: Still a bit confused about wash sales
Replies: 9
Views: 487

Still a bit confused about wash sales

I buy $1,000 of stock. Ten days later, I sell $500 of it at a loss. Do I have a wash sale? My CPA says no because I haven't purchased "replacement shares"; I am merely selling the original shares I purchased. However, this doesn't seem to jive with the "no purchases 30 days before or ...
by johnanglemen
Sat Dec 29, 2012 2:19 am
 
Forum: Investing - Help with Personal Investments
Topic: Still a bit confused about wash sales
Replies: 9
Views: 487

Re: Short-term loss in muni bond fund

JDCPAEsq wrote:How much do you have to go to the trouble of realizing a 1.5% loss? Hardly seems worth the trouble and risk unless you have a sizeable six-figure holding.
John


I wasn't intentionally harvesting. I needed to sell to cover a tax bill by year end.
by johnanglemen
Thu Dec 27, 2012 9:39 pm
 
Forum: Investing - Help with Personal Investments
Topic: Short-term loss in muni bond fund
Replies: 7
Views: 381

Re: Short-term loss in muni bond fund

You can deduct the loss if you have held the shares more than six months. If held less than six months, you can only deduct the part of the loss that is greater than the tax-free interest you received. SInce you only had the shares for three week, you would have received only a minimal amount of in...
by johnanglemen
Thu Dec 27, 2012 8:33 pm
 
Forum: Investing - Help with Personal Investments
Topic: Short-term loss in muni bond fund
Replies: 7
Views: 381

Short-term loss in muni bond fund

I don't quite follow the rules around whether or not you can claim a short-term loss in a muni bond fund. Say I bought VCADX on 12/5. Then I sold some of it today at a short-term capital loss, since it's fallen around 1.5% in the last three weeks. Is that a 'real' deductible loss or not?
by johnanglemen
Thu Dec 27, 2012 8:17 pm
 
Forum: Investing - Help with Personal Investments
Topic: Short-term loss in muni bond fund
Replies: 7
Views: 381

Re: When are funds available after selling a Vanguard fund?

livesoft wrote:Let us know how that wire goes. Will you have your funds at 9 am or at 4 pm?


9am. Not that it matters. The day was my concern.
by johnanglemen
Wed Dec 26, 2012 5:19 pm
 
Forum: Investing - Help with Personal Investments
Topic: When are funds available after selling a Vanguard fund?
Replies: 8
Views: 377

Re: When are funds available after selling a Vanguard fund?

Cool, Vanguard said they'll wire them out for free the next day so no need for Wells Fargo.
by johnanglemen
Wed Dec 26, 2012 5:12 pm
 
Forum: Investing - Help with Personal Investments
Topic: When are funds available after selling a Vanguard fund?
Replies: 8
Views: 377
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