Great comment! I've often pondered whether I could live aboard my little 24' trawler. I determined it could be done if I significantly downsized and simplified my life (not a bad thing) but I'd have to live alone. I'd enclose the aft with canvas/sunbrella. I already have A/C, shore power, water, a head, and ample storage. Showers would be a challenge though--perhaps I'd use the marina showers or install a water heater on board and use the aft wash-down sprayer.
Matters I worry about are considerations for a live aboard on any-size boat. What do I do with my family heirlooms, photos, or collections? Where do I go if a hurricane approaches? Where do I stay during haul out and repairs?
I say go for it! Someone else mentioned Janice--she's a great example of someone who has done it successfully on a smaller boat.
Going solo is the key. I could do it alone on a boat that size by myself, but not even with my wife, we would drive each other crazy.
He should go in my opinion. If he gets 2 weeks down the road and he hates it, the Albin could be sold and he goes to a rental house somewhere. The injustice of this situation would be if he didn't give it a fair shake. My monies on him! I think this will be the time of his life.
There is someone on this site wanting to downsize from their Albin 27FC to something more trailerable. Perhaps you can do a swap. They get a smaller boat, and you get one that is more liveable. I have always liked the Albin 27FC, but it is not very trailerable (it can be done).
For a single person the 27 with a camper top available for the center section when inclement weather strikes would be very nice (IMO).
You'd both stay in the family of boats you are familiar with.