Buy and older Mac 26 and charter the carribean
I have owned a 1991 Mac 26 since it was almost new and I find it to be the best of all worlds for the trailer sailor.
It trailers with no ballast so you can pull it with a smaller tow vehicle and you can tow in hilly regions of the country.
The keel dissapears into the hull so launching and retrieving is easy. You don't have to back so far down the ramp like you do with a fixed keel. I'v seen a number of cars stuck in ramp slime because of that. I'v also seen many trailer wheels go off the end of the ramp because the boat needs 3 feet of water to float off the trailer. Also, a dissapearing keel makes beaching the boat possible.
The water ballast keeps the boat stable. I've sailed in winds over 30 kts and have never been knocked down. If it takes too much wind, it rounds head to wind, even if you fight it. I've crossed all of the great lakes and sailed the coast of Maine to the Florida Keys (in segments) and never felt that the boat wasn't up to the task.
I took my kids sailing with me (I'm harnessed, they in life jackets) on inland lakes since they were 3 years old. They tell me now that those were the best memories of their childhood. We swam off the boat,I cooked, I slept in the V berth, they in the aft berth.
In short, I don't believe there is a better family sailboat. If a boat is difficult to tow, launch, retrieve, and sail, you won't go sailing as often.