Hi Keen,
If this is any help , my experience with a 9.9hp outboard on a 26', I hate the thing.
Calm flat days it is great, but any swell and it cavitates. Trying to solo sail is a pain, as what Chariot said, you get to the mast and it cavitates.
I lost my main halyard one day in a pretty ugly day, tried motoring and ended up being blown onto a lee shore due to the wave action making it useless, there was nothing I could do to stop it, the CG thankfully pulled me off at the last minute.
On another boat again in pretty foul weather was motoring, prop cavitated over a large wave, the motor had worked off the bracket, jumped off, snapped the chain and disappeared at full noise into the depths.
Mine is offset to clear the transom hung rudder, so no prop walk or turning circle. A friends Davidson 34 can turn on a dime, I turn like a truck.
I go through fuel lines regularly, they go hard and leak.
I have adjusted the depth a few times, but when it is deep enough to not cavitate all the time, when raised I find I am skull dragging it downwind.
I would love to swap it out for a little inboard diesel

.
Good luck to you whatever decision you make, but take it from me, they have issues the same as inboards.