First off, welcome to the forum and congratulations on putting yourself in a great position to save for your retirement! Your savings rate ($100k - $120k annually) is tremendous!
I don't know enough about S Corps to chime in on that question, but I'll take a shot at the others.
saelen wrote:2) Besides the yearly 3k limit on tax loss harvesting and 401k deductions am I missing any other tax savings I should be looking into?
What do you have for Health Insurance? I would consider a High Deductible Health Plan (HDHP Wiki Article
). Having an HDHP would allow you to contribute to a Health Savings Account (HSA Wiki Article
) which allows you to tax-shelter $3250 as an individual for 2013. Many folks here continue to pay for medical expenses out-of-pocket, but save their receipts and view the HSA as a pseudo-Roth IRA.
How large are the unrealized gains in AAPL and BAC? If you make charitable contributions, you may want to consider donating some of those shares. This allows you to avoid being taxed on the capital gain for those shares.
saelen wrote:3) Currently all my investments are in the target retirement vanguard fund. Since the stock matches my desired stock to bond ratio I don't see it as a bad fit but I anticipate changing to potentially a 3 fund portfolio as I increase my taxable investments.
I echo John and suggest you check out that Wiki Article. You have more than enough saved to justify going down the 3-fund (or in your case 3-fund + I Bonds) route. By viewing your IRA, 401k, and taxable accounts as a single portfolio (not 3 individual ones), it makes it easy to see the benefits of putting certain funds in certain places. You will get access to Admiral shares at Vanguard which will lower your expenses slightly.
saelen wrote:4) Any other recommended investing opportunities besides the 10k yearly in I Bonds
Is your rollover IRA traditional, or has is been converted to a Roth? If traditional, I would suggest rolling it into your current 401k. That opens up the option of doing a Backdoor Roth IRA
. (NOTE: This option technically exists anyway, but doing a Backdoor Roth with an existing traditional IRA opens up those contributions to become taxed. It's much more efficient to move the IRA into the 401k first.) While a Backdoor Roth IRA won't save you on taxes now, it will save on those taxes when it comes times to withdraw the funds. Give the size of contributions going forward, the Roth will likely be a drop in the bucket, but I would still recommend it. You could make a $5,000 non-deductible IRA for 2012 (anytime between now and April 15, 2013) and a $5,500 non-deductible IRA for 2013. Once both are done, convert the whole lot (~$10,500k) to a Roth IRA. You will have to pay tax on any gains, but if you make those contributions within a couple days of each other and convert shortly after, that wouldn't be very much.
You can search the forum for *lots* of threads on the mechanics of how to accomplish this.
saelen wrote:5) Any other advice on where I should go from here? I spent the past six months researching on this website and reading some of the recommended reading books but still feel like I have so much more to learn.
Having a 90/10 AA is a bit on the aggressive side, even for someone at 27. I'd suggest a move toward 80/20 between now and when you turn 30.
EDIT: Forgot to increase 2013 IRA Contribution number