Padgett, you have lots of questions (no problem with that), so I will try to address them in order:
Scratches on the sides are likely just from opening and closing. Not a big deal.
Corrosion on the bolts is common. Do they look like they have serious rust? If not, they can be sanded and painted with Rustoleum. Even in Colorado, the lift hardware on my 2 year-old TM showed rust. Not bad, but discolored.
The mount on the side of the wardrobe is not a normal TM fixture. PO may have had a shelf, a caddy, or something else hanging there. Part of the fun of a unit like this is to figure out what you may put there, to make it appear like you planned it.
Tires are due to be replaced, simply from age, according to very large numbers of trailer owners. They age, even without use. I guess that applies to tires, and trailer owners!
A 2kw genny won't run the stock AC. You will likely need a second 2kw generator. BUT, I have read about people putting a hard-start capacitor on their AC, which negates the need for a second genny. But, I have not done it, nor I have I researched it, so I can't make any promises.
No, you can't access the interior while the unit is closed. But, it is simple to open, and you don't have to "assemble" it to get in to put stuff in the 'fridge, etc.
Your second "also" - I believe my sides are 3' tall. It is snowing now, so I am not going to go measure it. So, your chair could be about 3' tall. Someone else will have to give a precise measurement.
Finally, about your TV. I have owned Jeeps since '86. I had an '04 GC with the 4.7 v-8, and DW had an '06 GC with the 5.7L Hemi v-8. I just got a 2417, which is about 1000 lbs less than a 2720, loaded for camping. As soon as I towed the 2417 home (65 miles) with the '04, I started looking into replacing it. While it towed ok, I like to get where I am going, so I can enjoy the destination. Used the Hemi on the next trip, up into the mountains, and it did okay. Replaced the '04 with an '07 diesel GC (yes, they made them for two years), and it tows much better than even the Hemi. Fuel economy is better, too. All this to say, don't be in a hurry to get over a hill with the 6-cylinder. You say you take your time, but be forewarned that, in my opinion, you may be disappointed in the way the Jeep tows any trailer in the 4,000 - 4,500 lb range. Just because it is rated at 5,000 lbs, doesn't mean it will do a stellar job of towing that weight.
Hope this helps. More will chime in, to be sure.