For me, cosmetics are definitely a distant second to the seaworthiness of the boat. I would love to have a good looking boat, but I'm going to be working with a $4k-5k budget initially and impressing the SeaTow guys with how pretty my boat looks when they show up is not my goal.
I definitely plan on hiring a marine surveyor to inspect the boat. I'm not going to rush myself on this. I plan on starting to look for a boat in September and having it ready for the water by April. I figure that gives me all winter to do any repairs that are necessary.