Re: Sailing alone??
Is there any way that you can leave the boat setup on the trailer near the landing or on a mooring in the lake? Maybe someone near the landing will rent out a parking space for you, or even give it for free if they can use the boat.
I think that ease of setup is going to be really important if it is just you. Even some small 20'ers can be a real pain to rig. This could make you rethink how badly you really want to go sailing on the weekend if you know you have an hour drive then at least an hour setup and take down, and then an hour drive home.
I've seen quite a few people lose interest in sailing because it is just too hard to get out there.
I used to trailer a powerboat to the lake every weekend and now I'm spoiled by having my sailboat just blocks away at the marina. I don't know if I could go back to trailering. Not to put a damper on it, but consider finding a better way to get out there.
Is there a marina, sailing center, or a yacht club near by? These are less expensive than you think if you just have a small boat?