We decided to step up in comfort from sea kayaking.
Last summer we drove 1,200 km and almost bought a sensibly sized first boat; a 23' trailerable diesel pocket trawler. The deal fell through at the last second because while on the hoist we discovered it weighed almost twice as much as was stated in a Pacific Yachting magazine article written in the early 80's. (The surveyor figured it was a combination of the writer using the hull weight, plus somebody putting extra weight in the keel.)
We had bought a better trailer for it, but it wasn't strong enough. We hit the slope of rationalization at full speed and started crunching the numbers...selling new trailer for a loss...buying a stronger trailer...buying a stronger truck...plus the cost to bring the boat up to snuff. We ended up walking away from the deal, but the sting was lessened by a feeling that the Karmic Forces had a better boat waiting for us that we didn't know about yet.
When we got home we went and finally looked at a Sundowner Tug which had been for sale locally for three years. We'd never gone to see it because it was a much bigger boat than we felt comfortable getting, and it was a slam-dunk the price would have been way out of our league...until that trip down the slippery slope of rationalization!
We got along with the PO's son and PO's wife really well. The sea trial was perfect. We settled on a partnership where the son, who's a millwright and knows the boat inside and out, will stay on through the years and teach us everything we need to know from the batteries on up.
So, now we have our retirement boat 13 years early