If you have the right setup, towing a travel trailer is not a "chore." Personally, I enjoy it. I look at it as a challenge. And again, with the right setup you're not getting buffeted/pushed by semis or crosswinds. I could easily log 500 miles a day towing the trailer. Not fatiguing or stressful at all. Here, the 2500 makes a HUGE difference.
Moneywise - is a trailer more/less expensive than hotels? I'd call it a wash. I'd say they cancel out - campground nightly charge vs hotel, eating out vs cooking, mileage towing vs mileage not towing. We've done both, though we'd usually rent a house vs a hotel.
With regard to using a trailer vs staying at hotels - the benefits of a trailer, to us...
1) Not having to deal with check-in/check-out times, rooms being ready, housekeeping, etc.
2) Not having to eat out EVERY MEAL. Homecooked meals are nice when you're on vacation. We pre-cook and freeze a lot of meals, then just heat in the microwave, cook some sides, and eat. We also brought a gas grill which would tap the trailer's propane tanks.
3) Not having to constantly pack/unpack suitcases/luggage/etc.
4) We can stop ANYWHERE and have a meal/use the bathroom/change clothes. This is a big deal with 3 small kids. The only things that don't work off 12 volts are the microwave and A/C.
My kids are now 20, 20 (twins), and 22. They've each told me that they clearly remember and treasure all of the trips we took on our vacations when they were younger - Grand Canyon, Yellowstone, Colorado, Utah, Gulf Shores, Washington DC, Colonial Williamsburg, NYC, Boston, Florida/Disney. Hell, we've probably traveled to at least 35 states, if not 40.