Since you have a popup TC, kayaks on the roof should not be that hard to load. My roof is about 11' up and I prefer to trailer anything I cannot fit in a cargo basket.
I second getting a multipurpose trailer over one dedicated for a single use. Once you have it, you will wonder how you got along without one. I started with a lightweight folding trailer and kept it for many years before getting a beefier trailer about the same size that does not fold. Although I also have large enclosed trailer, I still use my multipurpose flatbed trailer just as often.