TL;DR - After cinching down the cover for the tent a few hundred times, the stitching for one of the buckles on one of the cover straps ripped out. I sewed it back together and everything is good again.
TL;DR - I replaced the rainfly on the CVT Mt. Shasta tent with one that had no Stargazer windows. It is so much better, and now dries (relatively) quickly when it gets wet.