We had a 28' Weekend Warrior (and was able to sell it before it fell apart - but that is a different story) and went to the TC - and have not looked back.
I understand your fears on jacking it up high to get it in the truck. I had the same fears. You will get over that in time.
I like how we can equip ourselves for our trip depending on what we are going to do. Going to play tourist? Hitch up the jeep and take it with us. Use it to drive around town (and not worry about unloading the TC and where to park the dually when we go out to dinner.) Going out and shooting sporting clays? Hitch up the trailer and load on the clays cart. Need extra stuff? Toss it in the jeep or the trailer. Want to get small and lightweight? Leave the jeep or trailer at home.
We have found the flexibility with the TC to be the greatest asset. The only thing I am going to adjust is to rip out the dinette and stick in a couch.