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<<<<Therefore, can I make my yearly $2000 contribution into the IRA created from these defined contribution plans, or, regardless of my future intent, must I keep all monies from my old employer's plans untainted?>>>>
<<<can I rollover those funds into the IRA originally created from the old 401(k)/ESOP funds, or must it remain in a separate IRA?>>>
Maybe yes
I had SEP and Schwab and they said they would tranfer it into my IRa right that minute.
Check but I would say yes
<<I thought about taking the stock>>>
My rule is always to take the stock, but to each his/her own.
<<<After being rolled over, are these SIMPLE funds eligible to be converted into a Roth?>>>
You would have to pay taxes on the distributions. Just like in IRA
<<<3) Can I convert the IRA holding the 401(k)/ESOP funds into a Roth IRA?>>>
Yes, but you have to pay taxes.

Call someone like Schwab and ask these questions. I think I know all the answers but I might be missing something. I think you can move all of it into a IRA or a Roth. I think if the SIM IRA is discontinue then you get to roll it. Whatever you do have the gaining institution handle the rollover.
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