Ancal wrote:1. What's the best way to simplify my portfolio so it better reflects a three-fund portfolio (total domestic, total international, total bond) without incurring large tax liabilities?
2. Should I move all my bonds into a retirement account since bonds aren't a tax-friendly investment? If so, how?
You'll probably want to consolidate the ShareBuilder and Lending Club money (as notes wind down, unless you can sell them at a good price) to Vanguard to reduce your number of accounts, except for the 5% "play money" you're allowing yourself.
As far as getting to a three-fund, we'll need two more pieces of information: the current capital gains in your taxable accounts per fund/stock, and the fund options in your 401k/403b. The ideal would be something like 30% Total International (preferably in taxable), 45% Total Stock (anywhere), and 20% Total Bond (preferably in tax-advantaged).
The reality will still be a little messy, for two reasons. First, if you have accumulated large capital gains, it may not be worth selling those in the taxable account. For example, if you have large gains on the S&P 500 fund, you might just get enough Extended Market in a different account to balance it (~80% S&P 500 + ~20% Extended Market makes Total Stock Market) rather than selling it. On the other hand, if you have losses, you can sell it for the tax benefit and buy Total Stock Market directly. Simpler.
Second, 401k and 403b plans will have more limited options, so you'll want to play to their strengths. Find the one or two best funds in them and allocate the rest of your accounts around those as far as possible. That's often an S&P 500 fund and a bond fund.
I'm also curious why you're not putting the maximum into the 403b plan when you've got the money (see taxable contribution) and you're in a high-tax state. It takes some truly awful fund choices to outweigh the tax benefit, and it looks like her plan has at least some decent choices.
Ancal wrote:3. Right now, I'm putting no money into any sort of IRA because our income level is too high for a Roth IRA and for the same reason there's no tax deduction for putting anything into a traditional IRA. But is there any advantage into putting money into a traditional IRA that I'm missing?
As others have noted, back-door Roth is your best bet. If your 401k options aren't bad, it might be worth moving the rollover TIRA into the 401k so you can take advantage of this option. Go ahead and make your 2012 contribution to a *separate* TIRA for each of you so you make it by the 2012 limit. Later, you can make your 2013 contributions and convert the lot.