Will this plan succeed in retirement?

[joer1212]

When I retire at age 50, can I rollover my entire Roth 401k into a Roth IRA, then start making withdrawals by claiming the IRS 72(t) rule to avoid the 10% tax penalty?
Similarly, can I keep my 457b plan with my employer indefinitely after I retire at age 50, and start making withdrawals from it (which should be penalty-free, since it is a 457 plan)?
If I do both of the above, can I keep a part-time job (less than 40hrs), or sell my artwork? Or, will this trigger a 10% tax penalty in both, my Roth and 457b?
Lastly, if I start taking distributions from an annuity at the same time I am doing all of the above, will this affect anything?
FYI: I am 42 years-old, and I live in Brooklyn, New York.

I currently work for the MTA (New York City Transit) as a motorman.

I am counting on investing in the MTA deferred compensation plan until my portfolio is worth at least 500k. Then I will leave my job and live off the interest of my investments.

However, before I invest heavily in the deferred compensation plan, I need to know that I can start taking distributions from, both the Roth 401k, and the 457b plan penalty-free at around age 50. If I cannot, I will simply not participate in these plans, and instead invest my money on my own, after taxes.

I'm an artist, and I plan on selling my work to galleries or street fairs when I retire.

Also, while I don't plan on keeping any kind of job after I leave the MTA, I need to know that I can work a day or two (doing something easy like security) should it become necessary for any reason.

[ksoto]

I'm planning something similar. I am 54 an plan to retire at 55. I should have enough dividend income from a taxable account to provide about one half of my expenses. I may be able to make up the rest from a part time job/business I started about a year ago. But as a "plan b" I can take IRS 72(t) distributions from an IRA. I have a 401(k) and several IRAs. One of the IRAs should provide the required income stream using the "amortization method". Because of my age I will only be locked into the distributions for 5 years. I like this method because it allows a larger distribution and it is calculated once and the same amount is distributed each year. Should not be a problem over 5 years. You may not want to be locked into the same amount for 10 years.
From what I have read there is no restriction on working and having income while taking the early distributions. You can even make contributions to ANOTHER IRA while taking early distributions. There is a lot of information here:
http://www.retireearlyhomepage.com/wdraw59.html