Re: Smallest sail boat you would take offshore?
Some masts are 'keel' stepped, meaning they go through the coach roof. Ours was stepped on deck. We could remove and replace the mast with only sailboat hardware and 3 people. It wasn't fun, but it is possible.
We weren't retired, just adventurous. We both worked odd jobs during the hurricane season (June thru November) and spent the rest of the year traveling. On average we spent about $175/mo. When a sailor sees something for the first time, he is usually thinking, "I wonder if you can eat that?" Seriously, you can catch/find almost all your food if you have a mind and the wind is free; we always anchored instead of tying up at a marina.
And by the way, we did launch and retrieve at the lake with the rig in the picture (4WD), but on most occasions we would have the boat lifted on/off the trailer.