DriverDan, I think you pretty much have the pro/cons figured out. You need to decide what tradeoffs you want to make. I have owned 3 popups and one hardside. Currently popup and will probably stay with popups. I like the lower height and don't need or want all the extras that usually comes with a hardside. I leave it on year around and even removed the jacks. I have close to the setup you have but my 2000 F250 is only 2wd. The 7.3l hardly knows it is back there.
The one extra to add to your list is if you don't have or want air conditioning the popup has much better ventilation for natural cooling. We have a Maxxair fan and seldom miss AC. I can run the Maxxair for a long time on battery, air conditioning requires AC, either a hookup or a generator. Lots of places I camp have no hookups and I hate listening to a generator.
