Thanks all for the input so far! I've been either Diamond or Gold with Hilton for approx. 20 years and gleaned a lot from the comments posted above. Most of the properties mentioned in this thread are new to me and the personal insights are greatly appreciated.
Arlflyer: We're flexible, and were hoping to learn of a fellow FlyerTalker's great experience. There are dozens and dozens of Hilton properties in Florida and the Hilton forum only has dedicated threads about a few of them. One property that is off our list is the Key West Casa Marina Waldorf Astoria - reviews in
this thread were disgraceful and horrific.
Please keep the suggestions coming!
Much thanks,
-Goat