This time resale will not be a consideration.
In the past I've bought with that in mind. During my sailing era I've owned several Catalinas. They're like Chevys. You buy them right, you keep them up, update a few things and viola you'll get most if not all of your money back.
First one was in 1992 when I bought a 30' For $18K Had an engine that got loose..... beat it back into submission, cleaned up the boat, bought some doodads, had the wife decorate it. (She's REALLY good at that.) Sailed it for 5 years and sold it for 22K
My last one was a 42' Bought it for 60K out of foreclosure which at the time was about $.60 on the dollar. It was neglected but not abused. Put three months of HARD work and $35K in to it, sailed 6000 miles in 5 years and sold it for $95K. There were 10 for sale on the bay that summer, mine was the ONLY one that sold. (During the survey EVERYTHING worked, but that only happened once.....

)
If I were to do the same thing now I'd find a steal on a Carver or Searay 500 with diesels that needed some help. Eh, no. Wouldn't want to be found dead in it.
Next year or two I'll get a proper "yacht". Still in love with the 53/58 range. Get it up to snuff, retire in 4-1/2 and divide my time between the house, the boat and the motorhome. Hope to have the health to enjoy the boat for 20 or so years.
And then I'll sell it for whatever it's worth. (Or let the estate worry about it

) And say for shids an giggles that would be next to nothing...... I'll get in a decent one around an hundred and a half, that's $7500 a year. I've spent that in a hotel in two weeks. And, I'll be spending more on docking/fuel/maintenance.
Nope, this one will not be an investment.