We went from a pop-up to a hybrid for the same reasons you are, especially the hassle of setting up a pop-up. We're on our 2nd hybrid since 2003. The first we had for 10 years and was in excellent condition when we traded it.
Let's first talk about maintenance. The bunk ends are vinyl covered and I've never really done anything special to them save for washing off nasty tree sap a couple of times. Packing up wet is no big deal. If the bunk ends are wet and it's not raining, just towel dry them off. The little bit of moisture left will dry by the time you get home. If it's raining when you pack up, just open them at home and they will dry off in an hour or so. As far as seals go just use a good UV protectant on them twice a year. The seals on our old one were like new after 10 years. The rest of hybrid maintenance is the same for any travel trailer, inspect twice a year, and maintain all caulking and seals to prevent leaks.
Many people complain about how long it takes to set up the beds. It's because they have the idea of "making beds". Not sure why the need for fitted sheets, this is simple for us. Lay out a flat sleeping bag, throw on the pillows and a comforter, done! Also, newer hybrids use cables to hold up the beds. Simply drop the wall and put in the shepherd's pole. Both beds take me about 5 minutes to open, and my wife about another couple of minutes to throw on the sleeping bag and bedding.
Our setup time was cut in half with our first hybrid. If not for novelty lights and a bunch of whirly gigs we can set up our current one in less than 30 minutes.
Make sure not to look at the "dry weight" of trailers. Look at the GVWR. That'll ensure you stay under your rated capacity.
Being that you have 4 of you a 17-19 foot hybrid might work, depending on floor plan and weight. Our first hybrid was a 17ft model and it was fine with 3 adults. Like you we spend most of our time outside. If the kids are old enough, you could also consider putting them in a tent. Kids LOVE that.
I think a hybrid would serve you well. You are already used to sleeping under canvas, which for some is a deal breaker because you do hear all the outside noise.
I will also say that you have posted this in the travel trailer forum so you will get a lot of response weighted toward a TT. Not necessarily bad but know that many people who have objections to hybrids have never actually owned one. They aren't for everyone, but they are a great way to get a lot of trailer in a small package. And just because hybrids have vinyl covered bunks, does not make an apples to apples comparison to a pop-up. They are very different animals.
Have fun looking!