PDEMP, please post an issue only once. See my answer here:
"less than $20k on this upcoming purchase."
Late model used and well cared for older TT's are often good values. They may be better value than cheap new ones.
"I also have a nice little 2200 Generac Inverter generator that could be useful with a small trailer but I'm just not sure exactly which applications would suit it best."
The 2200 is a good size for a small TT. It can charge batteries, run a microwave, and even an RV air conditioner. Otherwise most stuff runs from batteries. It will run one heating appliance at a time or one cooling device. With a little energy management and/or small modification to the A/C you may be able to run two devices.
I found greater battery capacity to be more useful for dry camping. I have a small generator I bought 10 years ago. I have never used it except to test and service it.
I have a pair of 100 amp hour AGM batteries that allows me to dry camp for 5 days in summer and 3 days in winter. (The furnace uses quit a bit to run the blower.)
I wish you good luck and happy trails ahead!