- Did the previous owner tell you anything about the wheel bearings? Do
you see something like this in the centers of your wheels?
http://www.bearingbuddy.com/ Or, do you just see a metal cap?

There is a plastic cover over them. Is that adequate since it is exposed to
water so little?

- Before it's too cold to work outdoors without gloves, take a good look
at all wire junctions. Make sure all splices look clean, not corroded. If
they're made with electrical tape over soldered wire joints, that's sloppy
and they should be replaced with crimped connections covered with heat
shrink tubing.

Yeah, they are all covered with electrical tape that is falling off; expect
the connections are pretty bad underneath also. Wouldn't soldered joints
covered with shrink be okay? I did that for my invisible fence 15 years ago
and they are still okay. But it is probably easier to crimp them anyhow if
that is better.

- Spare ti Got one? Is it secured to the trailer with a cable lock or
some other method?

That's funny actually. Before pulling the boat out I checked and found the
spare was flat. Fortunately it held pressure okay; but the bigger problem
was that it was locked on and I didn't have the key! When I put the boat in
I didn't have the key either, and the tire was probably flat then also; good
thing I didn't need it. Came off in 2 seconds with an angle grinder.

What about propping the front up?!