Has anyone had success negotiating an upgrade directly with the hotel (or upgrading to a villa by some other means)? I've read several travel blog posts in which the writer says he or she did this (one was even upgraded to a two bedroom villa, but I suspect that was because she was a part of a special promotion).

I'll be taking my mom there next year around the anniversary of my dad's death so she won't be sad, and I'm using 60k Marriott points/night for a 5-night stay in May. I assume that's low season so I shouldn't have too much competition for upgrades, and I have Lifetime Platinum Premier Elite with Ambassador status, so I think I should have a decent chance at a regular upgrade. However I would prefer to get the villa with the private pool (since my mom would prefer that to one of the shared pools). I wonder if it will be possible to use extra points to upgrade to a suite, and then use the suite upgrade certificates to upgrade to the villa? Perhaps no one knows for sure yet since we still dont know how Marriott will handle using points for non-standard rooms. If anyone has insight I would greatly appreciate it. Thank you!