OK I just sold my 98 tj so here is my thought. Jeep too small, f350 too big. I found the tj too small for 2 people for more than a day or too. But wow, sweet truck, does that fit on the trails? I think it will and would make a nice overlanding rig.
It depends, what type of terrain will you be going through? Also,off-road Jeep parts will be much easier to find compared to Ford off road parts. Give us an idea of what kind of terrain you are going to be out on and you'll get a much better answer because these two options are like comparing apples to oranges.
I'm not completely sure in the terrain. I love the Rockies and want to take some trips out there and some day up into Canada. I've been camping in Colorado since I was 11. I know little bit about the terrain there. Really wanting to go to Montana and Wyoming.
My bias opinion would be sell the truck and get an adventure trailer with an RTT and all the goodies. Or sell them both and buy a JKUR. But really, depends on what you want to do. If you're really wanting to go off the grid then as stated, the truck is too big. But, the 2 door without a trailer leaves little to be desired when packing gear. Personally though, if you can swing it, keep them both and use the vehicle that best suits your needs for the type of adventure your about to go on.
I have thought about selling both and getting a JKU. But my family has a farm and cattle and I use the truck a lot for work. So that's not really an option yet. How hard is it to build a trailer? I have a 6x12 trailer that just sits around and isn't used.
I've used a number of vehicles over the years and it is a matter of how and were you want to use them. One of my most memorable trips was 10 days in a YJ with the wife. We went to Prince Edward island from Bangor Maine. We had a great time and really enjoyed being able to drop the top and run around when it was unpacked. The key was packing. For trips with the wife, daughter and dog we used the roof rack. It is amazing how much stuff you can load up on it.