I agree with the trawler idea, I just would never own one myself, something about displacement hulls doesn't really get my blood boiling.
But for your purpose I think It would be great.
Honestly when I looked into this, I was looking for a mid 80's to early 90's sport cruiser or aft cabin MY with diesels. The gas boats are much much cheaper to buy, and you can get rebuilt motors pretty cheap, but when it comes to resale they are at the bottom of the barrel.
I am more mechanically inclined, so I am not shy of engines, drives, or anything else. I know NOTHING about sail boats, other than they have a bunch of ropes and once again, are displacement hulls.
I would imagine if you lived on the boat you would be using the boat. I know if I did I would be cruising the bars during the week to find a hottie to take a weekend trip with.