I have hooked up my TT's for many years without any help at all, mechanical or another person. It becomes easy after a few times. But yes the FW is easier to connect.
The only downside I found with hitching the TT was lifting and installing the hitch into the receiver. It's heavy. Once at the campsite and unhooked I took off the bars and left the hitch in place until the trip was over.
I also discovered a short TT is more difficult to back up than a longer TT and a FW is even more difficult to back up. I'm not saying any of it is hard or impossible but the 35' TT was the easiest to back into a camping spot. The FW is vary unresponsive. I have yet to get it right on the first try.
The FW is the most difficult to level if needed.
The FW is taller so tree branches are always a concern.
After reading several of your posts I foresee either a Lance or Nash being towed with your GC in your future. It seems to make sense for what you are wanting to do, offroad in comfort. Find a TT that won't tear up your Jeep, find the floor plan that works for you and go have fun.
For us the floor plan has always been the top determinant, what works best for us at this stage in our life! When you walk into yours you will know it.