If I were considering moving up from a popup, and lived in New England, I'd be talking to this guy: This setup is literally turn-key, everything you need is there. Seems well cared for, by what appears to be a Roo/Shamrock enthusiast. I ran across his ad on Forest River forums, took a chance and found it on Craigslist...
2015 Flagstaff Shamrock 19 What's not to like?
I agree with the others, if the tent camper has been satisfactory to you in concept, the right HTT would be the best next step. Also if you only camp 2-3 times per season, seems difficult to make a big investment. Using use the Aspen, you'll want to watch the weight closely on the traditional travel trailer. This HTT even comes with a weight distributing hitch setup included!
Edit: PM sent...