Because you have towing experience, and you have done some pretty good checking too, you have realized that it's close to maximum capacity. One thing to consider is your hitch, and you will want one that is well rated.
The trailer is long, it's tall, and no doubt it's beautiful too. Five weeks of gear, including everything you and your lad will need, weighs a lot. It sounds like you enjoy staying for short times, and moving on. My guess is that you are going to be able to do it, but you might not like driving it. It's really true how when you get close or slightly over the limits, driving goes from a relaxed time, to the "white knuckle" feeling when the tail seems to wag the dog and you are clenching the steering wheel.
If you buy the trailer and the driving it difficult, are you willing to move up a notch in your tow vehicle?
