I haven't towed anything behind my Jeep, but I've spent seven years towing trailers ranging from 1000 pounds to 30,000 pounds all over Alberta, Saskabush, and Northeastern BC. Yes, I know that 30,000 pounds (trailer and load comined) is too much to pull behind an F-550...but my boss didn't. I did some math, and to my Boss's credit the loads hauled in that trailer were reduced to an appropriate level.
I've noticed a few things.
#1. DOT's in Alberta don't seem all that concerned about one-ton commercial vehicles. Sure, if you wave a violation under their nose you're gonna get slapped - but they don't seem to ride the "little guys" all that hard. If they can barely be bothered to inspect commercially registered and stickerd one ton trucks and trailers, they're not likely to pull over a Jeep unless you happen to be in a convoy with a service rig. You sound like you pay attention to things like load securment, maintaining the electircal system on your trailer, and testing your brakes. If you take care of those, it's unlikely that you'll get harassed for slightly exceeding the GCWR.
#2. I've been through a few "blitz" parties held by the BC DOT type. I'm talking 10-15 DOT officer, a rep from Industry Canada, 6-8 RCMP officers, and I think that the Tooth Fairy might have shown up for that one too
. I was in a one-ton pulling a 5000 pound trailer loaded with dangerous goods. Each time, they asked me what I was pulling, asked me if I had checked my breakaway system that morning, gave my truck and trailer a quick glance, and sent me on my merry way.
From your post, it looks like you're using a tandem axle trailer to pull 600 pounds of gear. You may be using a framing hammer to drive tacks...but I've never seen your trailer, so what the frak do I know anyways? Most RC's and sherriffs will probably not get concerned if it all looks kosher. DOT's are probably better trained to detect "rules" violations...but their training and goal are focused on enforcement for commerical vehicles. Unless your vehicle is registered with a gross weight over 4490 KG, they probably won't worry about what you do (as long as it's not blatantly unsafe).