Thanks, Dean! We called MS today just to verify that nothing would change with the current reservations and she confirmed that they'd all be safe. For extra measure, when I send the final paperwork into DVC, I'm going to add a note to ensure they don't cancel any existing reservations, haha.
I'm not too worried about the gift thing now, either. The contract, point-wise, is JUST on the edge of possibly hitting the $28k amount, but that's assuming the FMV is $70 per point for OKW, and I know I've seen it sell for lower.
Sent in everything to OCC today, so here's hoping we get everything taken care of before our September trip!