Back to the 401k vs. IRA and Roth vs. Traditional:
Since I cannot predict the future, I'm not sure which one is better. There are simply too many unknowns--income in retirement, future tax rates, future capital tax rates, the possibility of the government taxing Roth contributions later, etc. I've run the math about 6 different ways, and can't come up with a consistently good answer.
Because of this, I have decided for now that I will be doing the following to hedge my bets:
Max out my 2014 ROTH IRA as soon as I can (projected around March, will sell some individual stocks to get this quicker)
Max out my 2015 Traditional IRA as soon as I can (projected around May)
After both of those are maxed out, start contributing to my 401k at X% to Roth, and (X-3)% to traditional. Reason for (X-3)% is that the company match goes into the traditional 401k. When I start to get a company match, both will get equal contributions.
The $5,500 to the IRA will reduce my taxable income so that most is still in the 15% range, the (X-3)% even further, and if my original assumptions prove correctly, I'll still have X% in the Roth 401k. I expect that within 5 years, I'll move the funds entirely to the traditional portion of the fund.
This probably isn't the best strategy, but with all the unknowns it is in my opinion the safest. I will not be able to max out my 401k this year due to my funding of 2 years of IRA's, but in the future shouldn't have any issue.