It's always a trade-off of some sort. Always will be.
We tented when the kids were growing up. I didn't care for tenting but I grew up camping with my parents (in a truck camper and then a motorhome), so I longed for the day when I'd have an RV. Finally DW and I got a Starcraft popup (about '99 or 2000) and took a 10 day trip. We didn't like the setup and teardown process, nor the canvas snapping in the wind and all that. So we sold it after the trip. Finally in 2004 we bought a 23' Rockwood travel trailer, and that was the way to travel. I've had a series of small TTs since then. It's great to be able to stop anywhere, walk to the TT, open the door, hop in and do whatever. No setup at all for lunch, a nap, or a bathroom break. At the CG it's just a matter of checking level, hooking water/electric if applicable, and starting dinner.
I always wanted to try an A frame, so I picked up a 4 year old Aliner Ranger 12 and kept it for a year. It was easy to tow, fast to set up just like they say, and super easy to heat/cool. My dislikes were centered in quality of the unit, a number of small, nuisance-type issues like the window that sometimes wouldn't close all the way and the door that always scraped the lower threshold. And the countertop sat too low for comfort (although I'm just 5'8") so my back would get sore just from washing dishes. So I sold it.
Unfortunately business has slowed and money is tighter lately, and I am (like you) transitioning to a new career... believe it or not, I am getting certified for teaching secondary math. For this summer I plan to use my molded-fiberglass Li'l Hauley cargo trailer to carry my camping stuff and for sleeping in inclement weather (it does have 3 small screened windows), and I bought a cheap Coleman Instant Cabin tent so I can try tenting once more. My big must-have purchase was a Coleman ComfortSmart deluxe folding cot, which feels surprisingly good (yeah, no more ground-floor bed for me!) and I can use it in either the tent or the trailer. For heat, I like using the Coleman BlackCat catalytic heater. I already had a porta-pot and a camp stove. The thought of a window A/C unit zipped into the doorway of the tent in hot weather has crossed my mind.
This setup will do me for a while. Eventually, though, I have my sights set on a small, molded-fiberglass TT. They tow almost as easily as a popup. Sturdy bodies. No seams to leak, so there's no roof maintenance and no way a water leak can cause structural damage (other than the floor). Jeff, you might want to have a look at a Scamp or Casita sometime; a 13' is less than 2000 lbs and might fit your solo needs just fine.
