We tow our TT almost 1400 miles each way to WDW. Our first year at the Fort in '04 we towed a big, heavy old TT that was probably too big for our truck. DH practically made himself sick from nerves. But that was also our very first time towing ANY camper, and we really didn't have the right tow setup either. On the way home the alternator died on the truck at 3am in Middle-o-Nowhere upstate NY.
We limped to a local diner that let us park overnight in their parking lot, then up the street to the auto parts store in the a.m. Luckily DH knows his way around under the hood, and less than an hour in the parking lot and we were on our way <whew!>
The past 4 years we've towed our lightweight hybrid down without any trouble. DH was still nervous the first year, but with the right setup and some more experience towing it in general, he was a lot less stressed. Plus now he carries a bunch of tools... and some spare parts too - just in case.
These days I actually do 90% of the driving, and that will include this year when we've moved up from the 21' hybrid to a 30'+ hard side TT. We've already taken it on a few test runs, DH has adjusted the tow setup and it pulls like a dream.
If your vehicle is sound, your tow setup is good, and you have some roadside assistance service, a longer trip really isn't that much different than a short one IMO.
Not sure if that helps at all, but good luck!