X100...get a lighter trailer or a heavier/longer tow rig. There are so many decent options for lightweight camp trailers these days, it's pretty cool, just not retro cool like you're maybe wanting. Too much steel and heavy wood in the old camp trailers, whereas most of lightweight stuff today will be aluminum, plastic, fiberglass, etc. Not only will they be lighter, but they should be warmer and tow better as well with modern axles, brakes, electrical, etc.
Brands I'd be looking at: T@B, Rove Lite, Escape Industries, Aliner, Intech, R Pod, Osprey, Airstream Bambi (if you're rich or have an extra kidney), etc
I've never towed with my EB, but I have loaded upwards of 1000# in the bed multiple times hauling inventory around for my business and it's not super fun to drive like that...not a huge deal for a 10 mile trip, but certainly not something I would want to do cross county, let along cross country. My '77 F150 tows significantly better, being 5200# empty and having a 133" wheelbase (versus 92" for the EB), and was my go-to tow rig for ATV's, moving, etc, though if/when I had something heavy to haul (forklift, excavator, etc), I'd borrow a 3/4 or 1-ton truck. Current tow rig is a 2014 F250 diesel, and it weighs close to 8000# and tows 12-14k pounds pretty well when properly setup and loaded.