I agree with your pros & cons Detour, and I too feel your pain.
My brother and I have owned several boats separately, and/or as partners since 1976. We've had great times, and some not so great, for all the reasons mentioned above.
8 weeks ago, we both watched sadly as the new owner pulled our last 21' cuddy out of my driveway along with tons of boating equipment and spare parts we had accumulated over the years.
We have the time but no longer have the energy, ambition, or sometimes the $$ necessary to take care of the boat and enjoy it more frequently.
Even at that, my brother almost ran after the boat to change his mind.
The new owner called me a few weeks later and said after some elbow grease, he enjoyed it with his kids all day on Father's Day.
That made us both feel better.
We've been fishing weekly with a friend out of AHMM since early June. Also had two charters and a PB trip. We put fuel, bait and clean-up efforts into our friend's boat.
It's not the same. We're older now, but we still talk about one more bigger and more comfortable boat.........Our wives think we're two old fools.
We probably are. Who knows.
Weigh the decision carefully Bergen Angler. I would do it again for another 36 years if I had that amount of good boating / fishing time left, but that's just me.
Good luck & Tight lines.
Tom.