Cargo trailers and AC/generator setups?

Your 2000 watt generator should put out (about) 17 continuous duty amps. (2000/115= 17.39)
To be easy on your equipment, use a 10 gauge extension cord. In your described application, the 50' extension cord SHOULD be 10 gauge ("Extra Heavy Duty") as the safe/conservative solution. If you can get by with a 25' extension cord, a "Heavy Duty" 12 gauge (AWG) will work 'ok'.
http://www.homedepot.com/c/factors_to_consider_when_choosing_extension_cords_HT_BG_EL

 

or sell your eu2000 and pick up an eu3000

 

Or buy a second EU2000 and a parallel cable kit..

 

You can pair any of the Honda EU's together. Just cut off the female end of an extension cord and put a male end on it, and plug them into each other. Having two EU3000's, or one 3000 paired with a 2000 would be a sweet setup.

 

probably quite a bit.

As a teenager, I tent-camped for several weeks with a group of friends. I had my parents old crappy 1970's pup-tent. My buddies were paired up in '4 man' dome tents. They had rain flies, and I didn't. I rigged up a tarp to keep dry before a thunderstorm. The next morning, they were all awake half an hour after sunrise, baking inside their tents. I slept until 9:00. In July.

Shading the tent was a HUGE help. I have to imagine that shading the trailer, would be at least as helpful as insulating it.

Also - to hit on the plywood mounted window AC unit in the doorway of the trailer - I think this could be a really practical solution if you just frame a smaller door into the sheet of wood. You'd be ducking under the unit if you mount it up top, or you would want to build a little staircase to help you step over it if you put it near the ground (probably smarter for stability purposes), but mount some handles on the plywood, and edge it with pool noodles to act as an insulator/pad, and then just ratchet-strap the whole thing in place... No drilling or cutting.

 

Being a floor vent, wouldn't some critters love to make a nest in it?
Just a thought...

 

There's always this option too...