It depends on the pop-up. Some of them you push a button and wait 2 minutes for an electric motor to lift the roof. Some use hydraulics (not common, but you've owned a convertible, so you know they can be problems), but most use cables and pulleys with a hand crank.
The one my uncle had was a hand crank. Then you had to zip in the canvas and crawl into corners and put pins in the jacks. It took him 45 minutes to set up camp, while my tent and ez-up took me about 15. I used to tease him that it took him three times as long to get wet when it rains.
YMMV
My thing is, it gets old FAST. Like first time you're out camping, fast. There is the novelty of driving somewhere thinking you're getting better MPG (and maybe you are) and the novelty of setting it up for the first time. After that, it's work. If you save up and get a hard-side with a push-button lift, it's not bad... until the fuse blows, the jack screw strips, or a bearing decides to crap the bed. Having a full-on, non-pop-up means there is nothing about the box that can let you down when you get to the campground. Nothing is more frustrating than driving three hours only to find you have to get a hotel because a cable snapped, a motor fried, or a wire got chewed by a mouse. A hybrid or pop-up hard side with canvas has all of the downsides of a tent, plus added complexity and failure points. To me (my opinion) it's a lose-lose. I would much rather spend an extra $4 per 250 miles on fuel to avoid a pop up.
I'm not hating on pop ups... well, I am, kinda, but it's from my personal perspective. I just wouldn't sleep right if I said "go for it," and then had you back here in a year with a for-sale ad.
As far as weight, a 4000 lb slide-in is ridiculously huge. Let's take one of my favorite brands, Lance, and pick a random model. I picked a 2012 TC 850. fresh water, grey water, black water, bathroom with shower, propane, full kitchen and fridge. Aluminum frame, fiberglass sides, A/C, TV, Queen bed with two bunks. Dry weight is 2300 lbs and it gets you 18' of RV. Your comparison with the F100 is not going to be apples-to-apples. An F100 isn't even really a half-ton, it's closer to a crown vic with a truck body. You have a 3/4 ton "real" pickup with E-range tires, stiff springs, and 8-lug axles. I gotta believe that your payload is 3000 minimum, so even if you put 100 lbs of water, 50 lbs of clothes, and 50 lbs of food in it, that saves you 500 lbs for tongue weight. I certainly wouldn't condone going OVER any weight limits, but the truck itself I'm sure is physically built to handle far more than that safely. If you find that things are a little saggy or swishy, some helper springs can work wonders.
I think you're open to a wide variety of slide-ins with a fair margin of weight
Edit to clarify: I think if you had something like the Lance I randomly picked and filled it to the gills PLUS had a 5000-lb trailer, you'd be dancing around max GVW. Maybe a couple hundred pounds under or over depending on the trip, but if you feel more comfy with overkill, just pick a smaller camper.