We had a Coleman Williamsburg model pop up for 16 years. It was used 4-5 weekends a year as well as a 2 week vacation. It is a great compromise - low cost, easy to tow, gets you off the ground and provides some nice features. Set up takes a little while which is not fun if you are setting up in bad weather! They are great for sleeping but get tight on rainy days with 2 adults and 3 kids. We often set up a large canvas tarp outside over the picnic table to provide additional space.
We loved the pop up and it made many memories for our family. We have moved on to our toy hauler now that we are empty nesters. Kind of funny - much more room for less people!