we've got a year or two before pulling the trigger as well.
I know for sure that I don't want any canvas / pop ups. Many of our trips are not pack go, stay, come home. They're more like about hitting up a bunch of places on a 2 or 3 week trip.
The pop up makes it not much different than a tent when it comes to dealing with rain and packing wet.
Friends of ours just replaced their pop up with an R-Pod. They advised if you're going to get a pop-up, you should have a place to store it inside. Somehow, overtime they got a tiny leak and things got damp inside.
If they wanted to head out camping, it meant opening it up and cleaning the entire thing / airing it out, prior to leaving. So they didn't camp as much because it was a PITA.