Hi, Nick. I live in southwestern KY; got certified back in early '06. I'll toss a few random thoughts your way.
If you have an interest in diving in the Caribbean, a trip to Bonaire, with 1 week stay, unlimited shore diving, a rental truck, resort stay and airfare tends to run me around $2,000 per person. If you do a forum search for 'drrich2' and 'Bonaire' you'll probably some of my trip report threads, which use photos to make the read enjoyable and not a hassle.
Some people go stay at a hotel or resort in Cozumel and hire a boat charter to take them out for about 2 dives per day, and I guess mess around Cozumel the rest of the day for a week. I haven't priced it, and it's vary with where you stay, but I suspect a total trip price could be similar.
The SeaSoft Sunray is a popular, high-quality scuba boot that wears a lot like a sneaker, from what I understand. They don't come in my size (15), but my wife & a friend both like them a lot.
Pennyroyal Blue Springs has a fairly large shallow section that used to be a parking lot, but there's a thermocline around 15 - 20' in my experience, and if you want to dive on down, bring a wet suit. Part of this quarry is very deep. They've got a web site online.
Oh, couple of things I've learned along the way:
1.) Always take a tank banger or functional equivalent. If one of you ever runs out of air, you don't want your buddy ogling a fish 15 feet off to your side. In the water you're just not off to the side, in front or behind, you can be several feet higher or lower, and especially in limited vis. it's easy to lose your buddy.
2.) When shore diving, especially in rocky entry sites, walk out into waist deep water before putting your fins on, and take them off there on your way out. If you try to 'duck walk' into (or out of) the ocean shore diving in Bonaire, you can hurt yourself. In fact, you might accidentally bop your wife with your camera holding hands trying to get out, and she might get upset, shout an expletive and throw a fin at the beach...but no, that'd never happen...
Richard.