I think the standard is a no brainer. You write it off as 25% now and take it out at <10% (assuming your taking out <100k/yr). Thats hard to beat. The key of course is taking the extra 4k or so that you have by doing the standard and investing it.
The downsides of the traditional
a) you don't get access to the principal until 59.5. See 72(t) or roth roll overs for how to work around that
b) RMD - Probably not much of an issue for early retirees. Even if you have a 2 million dollar 401(k) (in todays dollars), you are still only taking out 73k to start with at 70.5 and at 80 you only have to take out 106k. If you end up having to pay a ton of taxes, you should feel ok about it. The goal isn't to avoid taxes. It is to have enough money to have lived your life.
You can definitely make some assumptions that make the Roth a big winner (i.e. you are in a higher tax bracket when you retire. You average 15% returns for the next 30 years ,... ) or the traditional (i.e you can cash out the side account tax free and suck out a good chunk of the ira at <10%) but in most cases you get almost equal results. My general thought is that the roth maximizes the amount of money you can end up with in the good cases.. The traditional on the other hand makes the worst case a bit better. The math switches a bit more to the roth as you get younger (i.e all those capital gains are tax free) versus older (you will not have as much capital gains on the contributions and you get to take out those contributions at a lower rate) but it is pretty minor.
I sort of like hedging. You contribute to the ROTH IRA and the traditional 401(k) every year. You are covered to some extend no matter what they do to the tax law.
I would pass on the ESOP but a lot depends on the exact plan terms. If you didn't work for the company, would you want to invest that amount of money in 1 stock and would that be the stock you picked? Now if they are just matching your contributions with stock, think of it as potential free money.
Ok so brief story:
I'm 27 my wife is 26 combined we make ~135k pre tax. i had always been of the mindset Roth 401k and Roth IRA are better is this really true. I have access to both i also have a company ESOP which ~ to a standard 401k. I am maxing out my 401k and IRA every year. Should I be putting this money into a standard 401k. My wife only has the standard option. (talk about a first world problem - roth or standard). My plan is to start a cash account following this year. but my thoughts were since its a roth 401k it rolls str8 to a roth IRA and now i have all the money i've put in that i can with draw tax/penalty free. Is this the correct line of thinking or should i be splitting up my 401k contributions more evenly or go pure traditional for the tax breaks now while we make so much.
Current life plan:
drop to 32 hour weeks in 4-5 years retire in 10-13 years before i'm 40. currently well on my way to doing this. assuming we dont hit that kids road bump to hard.