When living aboard, especially if it is going to just stay in a slip, I'd lean towards comfort over aesthetics. Straight walls (compared to a curved hull) give you more space in a similar footprint. I like the premise of a houseboat or floating home as a domicile. With a CD-25 tied alongside for when you feel the need to cruise.
Solo on a 40' boat is a lot different from solo in a house, condo, or apartment. The idea of living on a boat is romantic; the reality depends on the circumstances. We enjoyed being on Wild Blue for months at a time, but it was handy to have the truck in the parking lot for supplies and storage. And being in a place like Friday Harbor made it very easy to walk to the store or a restaurant. Wouldn't want to be there, living on a boat, through the winter, though.
Jason has, indeed, been on an interesting journey. Not unusual to move up in size... but most of us spend a bit more time on each interval. :wink:
Having downsized after retiring, we found it wasn't a problem getting rid of stuff, as long as we have comfort.
Good luck with this next chapter, Jason.