I believe the cover would be easy to take on and off once you got used to the process. It did take a bit for the first time install so that is probably not a good measure. However, I never take it off. With my skin situation, I would probably install another cover even if I end up upgrading...
Bald here with a side of skin cancer so I had your same concern. I installed a cover which snapped into place and looks factory. The sun is a non issue after 2 years of ownership.
I had the windshield replaced in my R!T at the Lake Forest Service Center due to a chip which turned into a crack. They did a great job and worked with the insurance company to get the costs sorted out. I think it was around $1800 before insurance.