A couple of things, when you get into larger boats, most of them will come with inboards, which is the way to go. You will still see a few with the old Atomic 4 gas engine, but most will be diesel. Even if you find a boat with an outboard, you will soon find switching the motor from one boat to another will be a major PIA. We have a close friend you used to have a 26' with an outboard. He hated it and is very glad to now have an inboard.
I'd rethink your feelings on insurance. Not a good idea to forgo that.