Thank you for everyone’s advice. As I mentioned in the beginning of the thread, I personally felt it overkill. When you have trusted friends giving you advice like that, it’s always good to get a second opinion though.
I think your friend may have been pulling your leg. Who carries around a boot and boots their own car? Do you want to make the vehicle have the appearance of being abandoned or, at least, unsupervised?
Here's my suggestion: Buy the boot, stick it on the friend's car, and tell him you are just making sure nobody tows his vehicle away while he isn't looking.
I personally hate the Sirius Guardian service but I think here (if it works for you) might be all you need. You can geofence it every night and actually get a notification if it moves. a few months of this service would probably be your cheapest option and could make you feel good in a worst case senario type situation.
The odds of somebody bringing anything capable of stealing from a JT are low. Most criminals go after something quick not 37inch tires that would be hard to steal or not loading a 5k+ truck onto a tow truck they then have to part out.
The biggest string of vehicle thefts I hear about now are simpel things like catalitic converters from a prius of all things. Apparently the scrap value on them is crazy high, like in some cases more than the car it is attached to. its also something easy to remove and get away with.
Seriously, the Trans Am Trail doesn't go thru any areas that you should be worried about.
More people along the route are likely to say "Hi" and offer to help if you have a flat than are going to even consider stealing from you. Don't believe all the media garbage about us "good ol' boys and gals"
As others have said, be aware of your surroundings and don't stop in areas you don't feel comfortable.
If you are willing to spend money like that on gadgets, then you might want to play some offense, not just defense. Defense is locking your doors, alarm is set, kill the battery, lock the hood, lug nut locks and all that good stuff. But beyond the obvious, nothing is going to stop someone from taking it, like others have said.
Imagine someone did just take your Jeep. Do you have a GPS tracking device? That's the best thing you have when it's time to call the police. You install one you manage on your own, and you can see it's location with your phone. Or you go the route of a subscription based service where a company manages it, but I would rather just do it myself. I've read stories about people doing this with an old phone they hide somewhere. Plenty of "find my phone" solutions out there. Traveling with 2 people, 2 phones? Sleeping the night in a hotel? Hide one of the phones in the Jeep overnight. Done! You might even be able to get some kind of notification in the middle of the night that your "phone" has moved, or detected audio. Just some ideas. I don't have the full solution, but I'm interested in researching this type of thing.