Since you live in a relatively flat part of the country you can probably get away with towing with a 300D but pulling a 2000# trailer up any kind of hill would surely put a strain on your transmission, especially a 20+ year old one. I'd probably say you should consider an extra cooler for it if you plan on towing frequently with it because that is really the greatest risk you run is overheating the fluid due to overloading it...but like I said it it mostly going to happen in hillier parts of the country I'd guess.
I guess it is a really good way to take a slow car and make it even slower. I'm glad I don't have to drive behind you
