What you call squirrely in your area, we call beat to crap where I live. :lol: Just going by the condition of the severely bent up fenders, the missing bunks and one bunk mount torn off, the hook of the safety cable straightened out and the missing hook from the winch, I'm gonna guess that it was involved in an accident that probably involved rolling the boat/trailer in some fashion. Trailer prices vary depending on your location but that would be too much for a trailer in it's condition in my area.
If you do decide to get it, I'd look the frame over thoroughly for any bends or cracks and be sure to jack each tire up and spin it, looking for warped rims or bent spindles.