FLU, generally speaking, it's better to rollover your 401k into a rollover IRA when you leave the company and then convert it to a ROTH IRA if you can handle the tax, than leaving it in a 401k. The reason why I say this is because you have much more options to invest in an IRA vs a 401k. For every fund type you chose in your 401k, I'm sure there are better performing one out there in the same category. The reason I say convert it to ROTH is because the $ you make will be tax free. Base on your past 11 years, that's a large amount of $ that would be tax free. I'm with you though on the point of automatic contribution. That's the easiest way to accumulate $ for the future with very little thinking involve. You tend to spend less too when you see that you have less in your savings/checking.
I guess I'm old fashion in this regards. I view having a vast area of fund selection a double edge sword. Yes, you have the ability to pick funds that are better than indexes. But at the same time you have the ability to pick funds that perform worse than the market. I don't have data, but I would guess most average people would end out doing doing just about the same as the market (being they probably are right and wrong roughly the same number of times over a long period of time). For example ,401k plans have boundaries on what can and can't be included in a plan. Perhaps it filters out a lot of good performing fund, but I would assume it also filters out a lot of poor performing funds.
Also, what I'm going to do when I have free time is figure out what my approximate tax rate was each year for the past 11 years, and figure out if I had done an after tax contribution to say a Roth (either through conversion or direct contribution), what the difference would be. This isn't entirely fair because Roth was relatively new, and roth contributions were limited to a some amount if you make above a certain amount. But for this exercise, I'll assume those limits don't exist. I think it's also a more fair comparison if you use a pre-tax amount to a 401k to match with an after tax amount to a Roth. For example putting $15k into a 401k isn't exactly fair comparison to putting $15k to a Roth. I think you need to figure out what the tax adjusted amount of $15k would be for your particular case each year. But what do I know about crunching these numbers..
