While looking up the locations of some of the areas in Mexico I was drug through as a child, by my hippy parents (yes in vw vans no less) I came across this:

Now for a consummate shoal water sailor, this area looks like the epic trip of a lifetime.
I’m no stranger to Mexico. However I haven’t been there in 40 years and a lot has changed. It seems much less safe now, for Americans visiting places off the beaten path. But if one had a terminal condition or something, this would be pretty tempting (ie nothing left to lose)
A small boat could be bought cheaply in Sandiego. Getting it through Mexico might be equally epic. I’m sure the roads are better now, but still over 1000 miles through varied topography towing a trailer.
There doesn’t seem to be much information on this area online. Just some short anecdotes which mention it in passing. The neaby gulf is subject to frequent high winds, but the whole body of water, and that to the south, is inland.
My idea would be to really barebones a cruise like that and be ready to walk away from the boat, or give away, and take a bus back to the states. The v22.2 , 21, or 25 would be good choices and all of those sail well and aren’t very expensive.
I was wondering about the procedure for entering Mexico with the boat on a trailer though. It’s a bit different than clearing in at a port of call and the protocol I’m sure is different. Is it regarded as just a motor vehicle? Maybe you have to do both haha.