I'm not a trailer fan so I cannot comment accurately. That said, I feel like for any rover that isn't one of these new fire breathing 300+ hp machines, you need the lightest trailer you can find. This is a problem since trailers, and off road trailers in particular, seem to keep getting heavier and heavier.
You say bears are you biggest concern. Keep everything in the vehicle and cover coolers/other containers that are synonymous with food. If a bear can't see it, they won't go for it. Also bears are easily scared off. A metal spoon against a fry pan is apparently very scary to them. Also being 14 years old, short, overweight, and using every curse word you know is also very frightening to a bear.
Go lightweight. Especially with an 88. Weight and bulky items are going to kill it. A Roof Top Tent is actually pretty awesome if you don't have any space restrictions and aren't taking the truck onto any difficult trails. Also you can keep all of your sleeping equipment up there. So no bulky sleeping pads, bags, tent, etc taking up room. But as mentioned before, its a giant heavy brick on the top of your vehicle.
People go nuts on the camping, etc. What I've learned is that when traveling solo, keeping it simple is nice. I use a jetboil, either to add hot water to something or to cook in/on. Works good and is compact. Sure I love my Coleman double burner stove. But I don't need that just for myself. Also its more that has to be cleaned.
As for the Series 3 itself, I've found a lot of issues are derived from having a crappy vehicle. When you get new tires, also get your rims checked. Bent rims cause a lot of issues, as I've found. Also upgrading the ignition and going through the carb make a huge difference. I replaced my rear axles to make sure those wouldn't be an issue. Also during inspection, I found the rear driveshaft was shot. Went through the brakes and steering as well.
I started daily driving the 109 just to work out more bugs. That has been extremely helpful and has allowed issues to be discovered 5 miles from the house instead of 50.
Dunno, just some ideas for you.