Glad to hear Austin is still diving. Wife and I dove with him around St. Kitts and Nevis from a windjammer cruise. I think the sites we did were Monkey Shoals and The Turtles. This would be back in 1998 or so I believe.
Back then he actually caught 3-4 lobsters and brought them up for his dinner....I remember joking with him that he should be giving each buddy pair one, and being told quietly by someone else that he was probably poaching by doing it on scuba gear. Ah well. He was a charming guy, and a great DM regardless (and his wife helped out then too..not sure if she's still in the picture?)
We're leaving for Dominica in 10 days (assuming American gets all their flights sorted out, although we're not scheduled on MD-80s)

We'll be forewarned about 'Dominica time' but we're staying on land and diving with Anchorage up in Roseau. Might take a couple with NID in Soufriere if that's not considered 'being poached' while we stay in Anchorage - I know we can shore dive from the hotel dock but would also like to do some of the closer shore dives and/or snorkel from Soufriere if we don't get down there on the boat from Anchorage.
I'd have to second many of the comments suggesting a liveaboard for you. You can consider the diving and the nightlife semi-incompatible, and just split them up: spend a week diving, then a week sunbathing and clubbing and eating out nice. Mom gets both weeks being pampered instead of just watching your bubbles from above.

No reason you can't mix it up a little with a land-based diving trip, but put plainly leaving diving as just a day excursion from the cruise ships means you're always going to get the short end of the stick because schedule rules uber alles. The ops won't risk going to the further sites, they won't get to dive with you enough to learn your likes/dislikes and do anything much about them, and you won't feel more comfortable about your own diving by only ever doing it for a dive or two, two or three days a year. On a liveaboard, diving up to 5x per day, you gain a lot more confidence in your equipment and yourself, your ability to break it down, can apply learning right away to subsequent dives, and you see a lot of other primarily DIVERS doing the same thing you can learn from. (Frankly I'm kind of surprised to hear about a guy with 500+ dives losing his fins, then fighting a broken mask strap...that seems like way too much bad luck for that much experience, and I freely admit I HAVE tried jumping off the boat without fins as well as dropped a mask. I don't claim 500 dives, either....this was with <20.

Since then I've rescued fins and masks, and when my own strap broke I shrugged, took it off, tied a knot in it and got it back on without interrupting the dive. Did get a bit of face-dentage from the effective tightening the knot caused though, and I now keep a small backup mask in a BC pocket as well as spare straps for everything in my kit.

) Regarding costs, you're spending the money for the cruise and then what, $100 excursion fee for two dives? A 3-day liveabout to the Flower Gardens from TX for example will run about $700, and that's your 'hotel', food, transport, and up to 11 dives in 3 days (5/4/2 is the usual 3 day schedule). So that's on the order of $15-20 per dive more than you're paying now, for WAY more dives, in the optimal locations based on the current conditions and experience of those running the trips day in day out (not based on 'getting back to port on time), and leaving time for the other part of the vacation. Not that there's a lot more to do in Freeport...but the Spree also does LA trips out of the Keys now (to the Dry Tortugas).
p.s. to ScubaTexan: haven't tried the FG since? You're missing out...great diving, close to home with no airfare!