We had our popup for 13 seasons, and we did 2-3 trips a year. Eventually time started catching up with it. We ended up selling it more for maintenance issues than the fact that we really didn't want to deal with the extra work.
Ended up buying a hybrid and we are so happy we did. Now, it can stay packed and ready to go for a short weekend trip. The camping season expanded from July and August to May - October. No midnight trips to the bathroom, a true kitchen, no cranking the roof every time you need to pack or unpack something...
We had to try to squeeze the new trailer cost into the budget, but no regrets. And, when we figure out our cost per night - its not too bad. Our youngest is 12, so we figured we didn't want to wait to take some of the longer trips we wanted to make with the kids. They grow up quick, and get busy with sports and school activities, so we thought the time was right.
Nothing beats a popup for low cost camping, so for one trip a year you could keep going with the current setup. If you want to get more use/enjoyment out of a camper, maybe upgrade or rent if that's an option. The hotel/restaurant every meal thing with kids doesn't get me excited, but it is an option.
2005 F-150 FX-4
2013 Rockwood Roo 23IKSS