I am definitely going to buy a used one, I dont want to go through the troubles and price of a new one, and like you said you dont worry too much about it as you would a brand new one. But I will be around 24/7/365 at the lake (most of the time
) So weekends would be enjoyable, but I would go out during the week also.
Mostly I will be doing the same thing you are doing, Fishing, joyriding, maybe exploring some of the smaller towns, and tubing/skiing. Fishing is the big part of why I want to be able to trailer the boat.