I've never owned a canvas popup, but I have done plenty of tent camping in all kinds of tents, including a Springbar, which was the only tent left standing in a windstorm at Flathead Lake.
I have a nice cot that I used when tenting it - no reason to sleep on the ground. I love the simplicity of tenting, but you can;t beat the comfort of a trailer when it comes to wet weather, as well as having a little more bear safety.
I currently have a Chalet hardside popup, and it's way better than a tent. I can put it up in literally about 3 minutes. I might suggest you sell your canvas one and get an Aliner or Chalet. It will solve most of your problems without losing the great gas mileage and towing ease.
