Good luck in your search. You dont have to spend a ton of $$ to have a great time on a safe, fun boat. I picked up a moisture meter when I was shopping, saved me a ton. Well worth the purchase.
I chuckled at your comment about boats not liking to be outside. My boat is either at the slip, sailing or in the storage yard so never under cover. Keep it clean and maintained and there's no issue. Being able to keep a boat on a trailer would be nice but you still need to flush the engine/drive, clean the bottom....
The work never ends but you cant beat being on the water.