"But I can get away with towing 1 with the right truck bumper? Would Gas or Diesel be better."
A newer half ton (Eco boost, current gen tundra, etc) can pull a single vehicle (4k rig + 2k trailer = 6k) just fine. Don't expect to run in the left lane up hills or win any mpg awards along the way though.
If you want to haul 2 rigs go with a diesel and a goose. There was a guy on Co4x4 who used to haul 3 rigs behind a 3/4 gasser avalanche and he survived. Actually, come to think of it I haven't heard from him in a while.....
I really like having a tow rig but if your jeep is built right and you know how to wheel it then it's not necessary. At your age I'd suggest spending your $$$ elsewhere but I'm not your dad. I've seen too many friends build a rig so big that it can't drive on the highway and is no fun on anything but the top 5 trails in Co, they don't wheel anymore because it's too much work to load it on the trailer, find someone that can actually hang with them and drive a few hours to that 1/4 mile trail that's actually fun. There's something fun about being able to drive to that local wheeling spot and just enjoy it. There's also something nice about being able to load it up, put the family in the tow rig and run that trail that's a few hours away.
I love my CTD but I know for how much I tow I'd have been thousands of dollars ahead, and only a few minutes behind, had I gone with a gasser.