Sorry if I am resurrecting this. I need your help on 2-3 options.

Note: Diamond status.

1) My grandmother's birthday is 3/11, and I'd like to take my grandfather and her on a little beach getaway on or near her b-day. I'd like to keep it to a 2.5 hour drive from their home in Boynton Beach (10 mi south of PBI). Anything from Cocoa to Miami Beach is in play including a very nearby staycation e.g. Singer Island. Extension of diamond benefits to a second room on the folio is a HUGE PLUS. I'd pay for a third breakfast, but if I can avoid it... I have had good experiences at Cocoa and Singer island on solo travel.

2) I am also definitely doing a Key West trip eith a growing warchest of points. I'm reasonably gay, and I understand that thr gay scene can be very fun during March. Points costs are 60k for the HGI, 70k for the DT, and 80k for the Waldorfs.

Paying 60k for an HGI rubs me the wrong way (I've never tried WA or Conrad). I know this is illogical in the context of luxury locales in peak season but still... The DT seems to be quite good with DIA treatment, but the location is sub-optimal.

I may or may not have either my friend or my special-kissing-friend with me.

This would be a 3-5 night trip. I may or may not camp at Dry Tortugas/Ft Jeff (I know, it's rough).

Given my desire to try a top tier brand, location preference, and relatively minor point cost difference, this leads to booking a WA. Unfortunately, my research suggests that the Casa Marina merely sucks slightly less than The Reach, the latter not inaccurately described on another thread as a Motel 6 on a beach.

Wildcard 3: Figure out a cash solution to Key West and burn the points on a better luxury gaycation getaway in FLL or MIA. I am very curious about the FLL Conrad. DIA treatment sounds excellent.

Options 2-3 are extremely date-flexible from end-of-feb to May.