In my opinion, many of the most successful transitions from sail to
power involve trawlers.

Same sort of speed, the feeling of a displacement or at least
semi-displacement hull in the water, some need (although much smaller)
to take winds and currents in account, etc.

Particularly if you go with a single screw trawler you must develop a
specific skill set to handle the vessel in an admirable manner, and
there is some satisfaction in doing so.

With high powered twin screw boats you can defy nature a bit and get
away with it more easily than with a slow moving single inboard.