Sounds like the timing could be off, but I'm not sure how. That was an issue with my blue truck when we swapped the motor--the timing was 180 degrees off and it wouldn't start.
The only way to go is up! I could take a couple of pictures of our topper/bumper racks that we have at work if you need ideas, but I’m sure you could get the concept without pictures.
I’d probably hang out in the non-cool crowd (MJs, XJs, the real Jeeps). The main reason I asked was to get an idea compare to the Back to the Fifties car show (10,000+ cars).
Or, you spend 15 grand making it legal and overland ready and you live in the Jeep, best of both worlds, with the exception of running water, indoor plumbing, etc., etc.,
I do have the 8.8 swapped into my truck. I used one out of an Explorer Sport Trac, so it was about an inch wider than a regular 8.8 and has drums. It was very worth it because I upgraded gearing while I was at it. No brake line extension is necessary with 3” or lift. You could probably do an 8.8 swap in a weekend if you had all of the parts already.
I love vice grips, especially the needle nose ones. They are also great at pinching off rubber fuel line so it won't leak. I'm sure it would work with brake lines too.
We have only been doing a Hybrid model (2 days in, 3 days out of school) for 1 week now. We went 11 months (including summer) strictly virtual. It sucked.
I think you should step back and decide what you want this truck to look like long term. We can help advise you from there. If you are going to do anything except keep the truck bone stock, or very close to it, then you should be looking at upgrading your whole axle. If you want to lift it and add big tires, you will need to change your brake lines anyways.