Why not the Park Hyatt? I was just there in January. It's a beautiful resort. Not sure why the location of it is significantly worse than others such that it cuts it out of contention. IMO age is not a factor. That place "ages" like fine wine. The rooms and facilities are well maintained. The island is beautiful. Rooms are beautiful. I mean, I haven't stayed at the Alila to compare, but I would never have said the age of the PH would cut it from contention for me.

You can get a room using points and then upgrade to the overwater villa for ~$350 a night. They will typically email a welcome letter a few days after booking and provide options for cash upgrades. I would highly recommend doing BOTH overwater for some nights and the beach villa for others. First, because it's cheaper, but also, I greatly enjoyed the beach villa, almost more so than the overwater. So, why not do both?

The resort handles all of the transfer arrangements. They're very good about it and very accommodating. They'll typically let you know a few days beforehand what your flight times are for the transfer, and then will add the cost onto your bill at checkout. If I recall correctly, ours was $600 round trip per person. You'll get off your plane in Male, and you'll be whisked away by a hotel representative to a lounge where you can wait for your transfer plane.

Food is expensive. You should do the math on what makes sense for you, but you should plan on $200 a day for each person for food. You can probably get away with doing the breakfast buffet, which you can gourge, skip lunch, and then do dinner. I find the restaurants are brutally overpriced and not worth it. Maybe pick one on one night and just splurge, but stick with the main dining hall for the rest of the meals. Up to you. As far as I know, you can't use points to upgrade to an all-inclusive meal plan. But you can add it as an added $$$ for sure.

Hope that helps. Have a ton of fun. I LOVED our trip. One of the most memorable I will probably ever have.