At this point, only one thought....please, please don't do this! You have too much trailer and not enough truck. Just a impression, but I'm guessing you'll be doing the driving??? Yes, it's pretty much easy, but not so much in an emergency. None of us want to be a kill-joy for your excellent plans, but also don't want to see pictures of you and your dear son and new TT rolled over on the side of the road or hit by a gust of wind or a semi and lose control. Another judgment, and forgive me if I'm wrong, but you sound stressed to make this happen with the perfect trailer. I think most of us would agree that somewhere along the line, we've had to give and take to make things work and be safe and SAFE is the key word. Never mind anything else. You have a nice size truck for something in the 25 - 28' range DEPENDING ON WEIGHT. Please don't even think of going over 1000# less in towing than your GVWR. Preferably more. Right now, by the time you add your son, some clothes, the food from a stop at McD.....you're likely overweight. That is so not good. You came to share your excitement and to get good and solid advice, so please heed what you're hearing. Re privacy....you can still maintain your privacy with some compromise. Bathrooms have doors. Many bedrooms have doors or curtains to pull. And in the real world, you've both probably had more view than was intended at the time. You don't need to be a bundle of nerves and need a bottle of Xanax by the time you arrive at the campground. You need a safe and relaxing drive so you can set up camp and enjoy your time together.
Re a 5th wheel, that might be a solution, but is it worth the bunch of $$$$$ to make the change from what you have now with a suitable, albeit maybe less than perfect TT to something you may find you don't care so much for after all. I would take baby steps here. Just be safe....that's our main objective.
Trailerless but still have the spirit
2013 Rockwood Ultra Lite 2604 - new family
2007 Rockwood ROO HTT - new family
2003 Ford F-150
4 doggies - We support Adopt/Rescue.
Sam, you were the best!
Cubbie, Foxy, Biscuit and Lily - all rescues!