Thank you all for the information- obviously we have so many different aspects to consider! I'm just now starting to learn the ins and outs of Flyer Talk and the traveling game.
I figured that $500 USD would potentially be tight, but it never hurts to have that as a starting point to reach for before looking at the other options (which seems that we might need to increase our budget or look for a less lux resort).
We definitely want to travel in early to mid October so I've been looking at the weather of some locations now, since we're just over a year out, to get a sense of what will be good and what we might want to avoid.
Have people used Virtuoso in the past to book? From researching it seems like they could be helpful avenues in knowing a lot of the ins and outs of certain resorts, but might come at a premium cost.
Really appreciate everyone's help in our search! We're so excited looking at all of the different options out there