Here's my 2 cents....
We had a pop up years ago. Enjoyed every bit of it. At the beginning it was me, wife and son. Then daughter was born. We ended up moving and ended up not using the pop up after a year or two and sold it. About 8 years later we ended up buying a 31' TT with quad bunks. Sone didn't live at home anymore, but we knew daughter would bring friends. After 3 years, no friends went camping. Last year, we decided to take the TT to the beach and store it there at a campground. They pulled it out for us and put it back. Great thing. We were spending a lot of time at the beach there so it made sense. Got rid of the truck and got my wife a new explorer. Bought a used pop up for a couple thousand that we could tow with the explorer and do more rustic mountain camping. We have always had our eyes on Class C's. One day I went to look at one at our local CW (where we bought the TT). It was a 28' model. Solid white and the floorplan was ok, but not all that great. They had ours sitting next to it, 31' model. Prettier color scheme outside and better floor plan. We wanted more of a room for ourselves with a full wardrobe and ours has it. There was a $10,000 MSRP price difference between the two. We were able to get either one for the same price and of course as soon as my wife saw them, she wanted the bigger and prettier one. I will say this....best decision of our life as far as RV's. We liked our TT, but it was not the best option for us. And pulling a 35' long TT down the road with an F250 is not the most comfortable thing. I can honestly say that driving the Class C is much more comfortable and there are many other reasons that it's beneficial.
As far as leveling goes. Unless you get one with leveling jacks, it's really not that bad. Yes, get you some lumber or several sets of blocks (or both!). It won't take much time for you to start figuring out what it will take to level it. We've used 3 sets of leveling blocks just to raise the front end to make level. I'm not going past that. If it won't level in the site no better than that, then i'm not staying in that site.
Don't say no to the tow dolly so fast... While the preferred method by many (especially fulltimers) is to tow 4 flat, for us weekend warriors, at least for us, it was not feasible to spend thousands on a set up of one vehicle to just tow it. My daily driver (07 Toyota Yaris) can be towed either way. But I was going to have to spend several hundred dollars on a base plate, hundreds getting it installed (plus they would have to alter the fascia on mine), then you got the tow bar, braking, lights, etc. A coworker priced it out for a Liberty he had and was quoted over $2500 if not more. Can't remember the exact figure, but it was high. Now if I went through all that on my car and then in a few months I get another car, I have to spend another $700-1000 getting it set up. I started looking at dollys. ACME is only about an hour from me. I started looking more and started sending them emails asking questions. We ended up buying for $1300 brand new with surge brakes. Pulled it over $1200 miles on a trip this spring from our home to Destin Florida and back. I was amazed how easy it really was. Yes there were some learning curves as i've never used a tow dolly before. But after hearing all the talk of how hard and how long it would take, I found out that it's hogwash. My initial set up was even in the rain! We can have it hooked and car on it in 10 minutes or so. And that's taking our time and making sure everything is straight. People talk about what to do with the dolly at the campsite. I pull up just forward of the site. Get out and unhook from the motorhome (car already off). I grab the handle and push it back to the back of the site (or other designated area of the site). I back up the motorhome and it covers about 2/3rds of it. I have my wife spot me of course. She's there to spot me either way. But it literally only adds a 2-3 feet to end of your RV. Get ready to leave...pull forward enough to where you can lift up on the ball hitch. Easy peasy. It's the lightest dolly made. It can be stored in the upright position (on 4x4 blocks). And I don't have to worry about which car. I have more of a selection of cars to tow on the tow dolly than I can 4 wheels down. Plus the dolly can be used for other towing if needed.
As far as the generator, ours is a 4000 I think. Will depend on the unit.
If you are thinking of replacing the 5er, then I would go with a little bigger Class C for the 4 of you. Also depends on your camping. We like to divide it up between resorts and partial/no hook ups. Driving one around without a toad will be more cumbersome and you need to not only thing of length of space, but your heighth.