We have a cruiser (33) that we spend summer on, and a houseboat (40) that we spend the winter on, obviously in different climates. There are pros and cons to both types of vessel.
I like the cruiser for the maneuverability, smaller transient dock fees (based on size of vessel), and classic boat look. They're easier to wash and go faster too.
However, the houseboat is more comfortable as a live aboard vessel, more storage space (need room to have and store a Christmas tree!), more entertainment area, and larger galley. Bonus, they make you slow down and see the sights.
If I could have my choice of vessel (not counting the choice of mega yacht with crew in speedo's fetching my margeritas) it would be a trawler, likely a Kadey Krogen.
http://www.kadeykrogen.com/44/
or a Great Harbor, which is a really impressive boat for it's size. (and American Made!)
http://www.greatharbourtrawlers.com/gh47.html
M/V The 69 Queen
1969 River Queen 40'
and a 24' Pontoon "Red Solo Cup"
Port of Fulton, MS