I thought it would. The problems I saw were:

1) storage when not in use. I usually stay in motels and was not willing to have a dedicated pop-up as my only trailer
2) difficulty of operation. When using the pop-up the boat would need to be unloaded.
3) additional towing weight and windage would not be economical.

On two occassions I've taken extended camping trips (around six weeks each time). The right tent makes all the difference in the world.