Hi Klaussic, I live in Slidell and belong to Tammany Yacht Club. When things return to normal (whenever that is) we could probably arrange for adult sailing lessons, and also get you aboard a few different boats so you can see what they're like in reality.
I was just wondering, have either of you ever actually been on a sailboat? I ask because some people just never get used to the way the boat heels over. As far as draft goes, around here less is better unless you are racing. 6 feet is about all you want, and 5 is better. A/C is nice to have, but if you want it when away from shore power, that is a much more complicated situation. It is just barely doable to run a window A/C from a portable generator, but I wouldn't recommend it, between exhaust fumes and having to carry gasoline on the boat. The best solution is a permanently mounted A/C system in the boat, along with a permanently installed diesel generator. Truthfully, that is probably not going to happen in your size and price range.
In the boat age range you are contemplating, I wouldn't get too hung up on specific brands. What is really going to matter is the condition of the particular boat you are looking at, and the level of upkeep it has had. This especially goes for the engine, which will be getting kind of old, and will cost as much as the boat is worth to replace. Water leaking into balsa cored decks is another expensive fix.
Whenever we can get out and about again, try to get in touch with some of us sailors at the yacht club (I'm assuming you live in Eden Isles) and we'd be glad to help you along your journey.