Okay, if it's an I/O you might get away with a single and a bunch of practice. Straight inboard, 10x as much practice and accept the fact that on some days you may not able to control it. You'll just have to dock with the pointy end in. My general advice would be to go with twins.
Pay attention to engine access and whether you (or the yard if you use one) can actually get in there to work on it. My last boat was impossible- the engine hatches were wide from side to side, but narrow from front to back. Pull a hatch, step down into the bilge, and.... now what? Can't bend because the deck is in the way, can't get to the rear half of the engines. When I had to have a Y-pipe replaced, the yard had to dismantle half the deck to move the engine. I paid for that in additional labor.
My Carver has BIG engine hatches. I, old disabled guy that I am, just replaced the entire cooling system on the starboard engine. Mani's, risers, every cooling hose, and did a full tune-up on it at the same time. Wasn't easy, but it was doable.
My .02
