Mrs. BD and I have a disagreement about boats. Maybe readers can offer us some marital help.
She wants a Great Loop boat, a trawler with a couple of staterooms, galley, head, shower, etc. She prefers these Beneteau Swift Trawlers to the Grand Banks trawlers. She wants to do the Great Loop (in bits) but I'd rather do the Appalachian Trail (in pieces, of course) as an adventure, since travel is sort-of out this year. Those big trawlers, I feel, are just too much boat for my comfort and skill (even with bow and stern thrusters). I could learn for sure, but do I want to? In fact, I am more comfortable with sail than power even though most sail has accessory power too.
I've had boats much of my life, and thought I was done with them. Less things to worry about makes me happy. Kayaks are great fun and good exercise, and zero worries. But when it comes to real boats, my preference is for jaunty Downeast-style boats. I can handle them just fine. They are ok for overnights, but not for lengthy cruises.
I kinda like this old Dyer 29
Pics of a couple of Downeast boats -