Sailing in the Gulf of Mexico and sailing in the Bahamas are significantly different types of sailing unless your just talking about taking the boat out for a sail occasionally. In the Bahamas your more of a cruiser than a live-aboard. True, you living on the boat in both situations but your location will probably vary more frequently cruising than in what most consider a more stagnant live-aboard. Some live-aboard never move from the slip... some actually can't!
What is it your looking for? Using the boat as a house or using it as a vehicle to get to new places or just as a sailing toy?
If your "Two Married Persons" means 4 people then a 36foot boat will get really small very quickly if all are not compatible and all have similar sailing interest. Any non preforming crew will soon become a problem for everyone. To some degree if your actually going to do serious cruising you will need to depend on the crew and a broken crew is a really bad thing that can occur quickly. While some things are very similar between boats and aircraft... the crew on a boat is far more active in most aspects and must be depended on at certain critical times.
My wife and I for the most part. Mostly getting to other places. I like to visit different cultures and do not like the commercialized version. I am more of a get back to the less traveled parts. Help a local villager re-roof his hut for some bananas type of guy.
I do not believe that you will have to depend on crew if the boat is able to be sailed alone. This would mean that if you wanted to take your elderly father you would not be able to. If you went with your 3 year old grandson he is not really going to be any help either. What I think you can not do is take off depending on help and then not get it.
I have vacationed with my wife for 31 years or so now. I have learned to not expect any help but if I get it great. Some of the worst vacations were when I expected her to make some decisions and she didn't.
Not really a sailing toy, I plan on Bahamas, Gulf, Panama canal, up Pacific coast, Alaska, Up Mississippi, around Great lakes up and out through Canada. Atlantic maybe over to UK. I had planned a flight from Canada, to Greenland and over to the UK. Fuel is getting too expensive now to do it.
I am looking at this more like the older couple that buys a motorhome and travels around the US. My US is just a little bigger.