I am very thankful for this message board. I have learned so much from it. I always appreciate the advice and opinions. I am new to all of this. I bought my 1st tractor even though it is a sub-compact I use it a bunch. Just like today I was cutting trees in the woods and after I cut the trees I pulled them up out of the woods to cut them up into firewood. Sure beats cutting them up and then breaking my back carrying the wood out. I bet my Dad sure would have liked to had one of these tractors when he was alive it would have made his life so much easier.
SCUT, CUT, Garden Tractor, or hand shovel - if you've got the right tool to do the work you need to do, you'll use it a lot. I'm glad that you're finding lots of useful things to do with the machine. Just don't push it too hard or you won't even have 50 hours on it before you're lamenting not having bought a larger machine.
s219 makes an excellent point about the construction of utility trailers (and I'll apply that to most landscape trailers as well). While they certainly can take the weight, their design "assumes" that the weight is distributed out and will have many points of contact. When you load a car on there, you're applying almost 1,000 pounds of weight in a roughly 1 foot square area (the tire's contact patch). That's rough on the decking, but it also makes it rough on the support members underneath. Many of them are made with simple angle iron (utility trailers especially), and that stuff isn't going to hold up carrying that kind of weight over such small areas.
Putting a solid deck down would help to distribute the weight some, but it's still likely to be a short-lived life for the trailer.
I just realized that you're looking to haul a Cherokee, not a Wrangler - those are even heavier (if you were going to take a Grand Cherokee, it's even that much more weight on top). When I was shopping for a trailer, I looked at things like the Carry On landscape trailer. If memory serves me correct, those were somewhere in the $2500 range for a 7k trailer. An equipment trailer was roughly $750 more. Those are prices for new, but you can see that stepping up to a much more solidly built trailer *can* be managed financially.
Since you seem like you're willing to take on some repairs and such, you may very well be able to get a nice 7k equipment trailer that would need a little work and be able to do an excellent job for you while towing.