That's a similar set up to what I am thinking as well. But in order to stay legal with an M211 in tow, the loaded deck height of the trailer needs to be about 30" to stay below the 13' 6" bridge height. Also, take into consideration your longest vehicle that you will be towing the trailer with... That will determine your maximum overall length, including trailer, which needs to be under a certain length. In Illinois, I have to stay under 55 feet total length, that leaves me 32 and some change to play with on the trailer.
Another thing to consider is your tires on the trailer. How common are they, what if you have a blow out and have already used your spare, can you get the tires locally most anywhere you go? Also, consider the load rating on your tires. Most of the time, your axles are rates higher than your tires, and your tires determine how much weight you can handle. The tires is where I'm at in my research. Even if I have to spend a little more to have custom steel wheels made to bolt up to the hubs so that I can have a more common tire.
One more thing to think about is you stare law on plates. I have residences in two states. If I plate my trailer in Illinois, I have to take in to account the max GVW that I will ever haul. Since I want to stay below 20,000lbs including the trailer to keep from having a special inspection done on the trailer, that means my trailer has to weigh around 6,000 lbs or less empty. At that loaded weight, it will cost me $258 per year for plates on this trailer in Illinois... However, Ohio only cares about the empty weight of the trailer, bringing me in at about $52 per year for plates in Ohio. Regardless, per axle weight ratings still apply federally, but I'll never have to worry about that because I'll never have 38k in tow, let alone that much weight on a single axle!
Long and short, read through your state law for trailers, both commercial and noncommercial. Mine was helpful in Illinois because it actually gives me the formula to figure out max weight per axle... W=500*(((LN/(N-1))+12N+36) where W=any group of 2 or more consecutive axles rounded to nearest 500lbs, L=distance measured in feet between the extremes of 2 or more axles, and N= number of consecutive axles in any group.