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I have a Tohatsu 6 HP sailpro on my Hunter 26. I can hit hull speed at 3/4 throttle so what
@kloudie1 said about a 3 or 4 HP is spot on. The smaller the O.B. the less gas they burn, the easier it is to take it home with you (so it won't get stolen) the easier it is to take it to a shop for repairs, the less squatting it produces etc. etc.
I opted for the 20" which is the "long" shaft version. They also sell a 25". I wish I had opted for the 25".
@Whatfiero1 mentioned hobby horsing but you can also motor sail and if your O.B. is a short shaft and is to windward, the prop will come out of the water when you heel. In an extreme situation like a T-storm micro burst, you can find yourself heeled over even with the sails down and again, if your O.B. is to windward and is a short shaft, your prop will come out of the water and you lose all propulsion. Not a common problem but not the sort of problem you want when other bad stuff is already happening.