Bullet One: Yes - it is strange but the easiest way is to think of the fact that the IRS gives a current year break up to April 15th for contributing to an IRA (I know we are not talking about an IRA in your case, but again it is strange), the IRS has laid out certain tax treatments for all similar types of "retirement funds" and thus theoretically uses April 15th as the beg/end of each "year" for situations like this. Make sense? So, you deferred last year, but your return applicable to last year isn't due until April 15th, so that is the "window" of how they are treating this. I know...
Bullet Two: Depends on the type of retirement investment - remember, this is being generally stated in this section by the IRS
Bullet Three: Correct
Lastly, YES, the 1099-R is the reflection from the IRSs' "internal reconciliation", so to speak, which is being performed by the "payor" as per the regs they must follow. Since it appears to me as though you did withdraw the $2100 based on your statements above, then that is all together different than a traditional situation where someone just leaves one job and goes to another, thus usually rolling over anything they choose. I hope that makes better sense.
