Further assistance with IRR transfer at end of 6 year commitment.

Enlistment date: XX March 2009
TPU requirement fulfilled: XX March 2015 (6 years)
ETS: XX March 2017

The local career counselor has informed me that I have two options: request transfer into the IRR, which may take many months of paperwork, or complete a reenlistment contract that reassigns me into the IRR effective XX March 2015, so it'd be guaranteed to be a lot quicker. Is there any reason I would prefer one option over the other, and would either one have any significant effect on my entitlements such as Montgomery GI Bill?
Original Post
I'm hoping you figured this out by now but:
Reenlistment with subsequent assignment to the IRR is not available to you. Per AR 140-111, table 2-4 line 1, you must be within 12 months of the completion of your statutory MSO.

It won't be any quicker; the process has the same approving authority. In fact it could be slower since these contracts tend to confuse people.

Neither will have any impact on your MGIB. The 1606 will terminate once you go IRR regardless of how you get there.

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