A few more update pictures:
I rewired the trailer. The old wiring was pretty loose and the wires were just twisted together and electrical taped. I soldered the wires and made everything nice and tight. I used zip ties to hold the wiring nice and snug to the frame. I also re-installed the lights and military data tag on the frame:
Next up was several house on the angle grinder again with the wire brush attachment. I knocked off all the loose paint and rust. I then gave the bottom of the bed, fenders, and anything else that was rusty a coat of POR-15
Next up was primer. It could have used a little more primer, but I ran out, so that will have to do. I also painted the hard to reach places with rattle can olive drab. I figured those would be the spots that would be hard to get with the air compressor powered spray gun.
I had to re-install the bed on the frame because I'm transporting the trailer to my parent's house this week where I'll paint it. I had some issues getting the trailer to fit on the frame and for the holes to line up, but I guess that's understandable since I dropped the bed once when I was moving it and and flipped it over twice to work on it. I'd imagine things shifted a little. With a little muscle, I was able to get it back on and bolted down with new grade 8 hardware. Pulleys are great!