My wife & I are empty nesters, I'm retired and she has a _very_ flexible work schedule. We got our teardrop last fall, have used it a half-dozen times, just today returning from a three day trip along the CO, NM border. Spent last night on the continental divide at 10,600" elevation.
We love the teardrop and have no regrets. Zero set-up, nice self-contained kitchen, and off-road capability are all huge. We don't rock crawl, but many western forest service or BLM roads would be impassible in a road trailer, and the relatively short length allows us to go places a typical travel trailer couldn't possibly go. 32" wheels match the tow rig (a lifted van) so we don't need a second spare. Yes, it's little, not a "standee", but we think of it as an all weather wood & metal tent, so that isn't an issue. And we don't KOA camp or stay in any kind of developed campground, so the (relative) lack of privacy has never been an issue.
We like that we are at "ground level", and not up top of a vehicle in a popup. First, we camp with our dogs, and being able to quickly address any issues associated with the dogs is important. They sleep in the van with a fenced enclosure around the open side door of the van for night time potty trips, but on occasion we have had to deal with visiting wild-life or with a sick (puking and diarrhea afflicted) dog and being right there is very nice. And secondly, the 30 mph wind, gusting to 50-60 mph on the divide last night had no impact on us. No flapping canvas or other issues.
So, no regrets, and no thoughts that we might have done better to purchase something else. The only (very minor) regrets relate to how we accessorized, or failed to accessorize, the TD, and we are in the process of fixing that as we use the trailer and figure out what is important to us and what isn't.
Best of luck.