OK, it looks like you're just trying to spend money. You've got a great base for exploration already, especially with the trailer, so get out there and use it!
For Michigan exploration and camping, here's my take:
1. Keep up on all preventative maintenance.
2. Tires (stock size or nearly so) + swaybar disconnects + good shocks will solve 99% of the needs for Michigan, save for Off-Road parks and a bit of Drummond Island.
3. A winch can be helpful, but I'd focus on waterproofing first. I've never had to pull myself with my winch in an "exploring" setting, but I have had more than one bow wave that ran up my hood and broke against my windshield.
4. Storage: build, don't buy. We have our TJ set up for week-long self-supported trips (minus gas fill-ups) for two adults, using a homemade shelf system built from OSB, an old bedframe, and a 110v MIG welder running flux core wire. It is solid, rattle-free, and keeps gear secured, organized, and quiet. It was built around our storage containers, and provides a friction-fit to keep things in place, and makes life SO much easier. Installs in >1 minute with four bolts in OEM locations.
5. Upgrade your lighting. Hella e-code headlamps, good driving lights, rear utility lights.
6. If you add a winch, use that as a time to level the front end back out (a spacer should be fine).
7. Consider Air-Lift rear air bags for load management, especially with a trailer. A saggy rear end is not cool, and bottoming out your suspension is not good. They still let you flex just fine, to the extent that it actually matters in MI.
If you've got the time in August, UPOverland2010 still has a few spots open...
My TJ Setup