I assume the boat has an outdrive, as most of the inboards I’ve seen have the starter mounted on top. But either way, I’ve always removed the outdrive ( or shaft) if I need to lift a motor more than an inch or two. And I don’t love getting underneath when the motor is hanging on a hoist. Had to swap oil pans on my American Skier last year; not a horrible job. I left the shaft attached, as I didn‘t need to lift very far. But with an outdrive, I can’t imagine you can move the engine up at all with the drive still on.
starters are tough. I don’t know how the pros do it. On my bow rider, I‘ve had the starter replaced three times. Once I had the shop do it, they charged me one hour labor, which means it took them no time. Once I did it myself, took a whole slew of wrenches - curved, offset, ratcheting - every option I could find. I don’t remember which one worked, but eventually got the bolts out. Getting the new starter bolted in was no pleasure either. Third time, I had the motor out, and went ahead and replaced a perfectly good starter, just to delay having to do it in the boat again.