If you use dielectric grease (dow corning 4 is my preferred product), it takes very little. If you see more than a change in reflection, that is more than you need.
Certainly dielectric grease is meant for the contact to contact interface. However, if you use the same rag to clean the inside and outside of the plastic barrel no harm, but do not leave any large build ups or "globs" (just to minimize dirt pickup, otherwise no harm). In some outdoor electronics / electrical work "packing" with some dielectric grease is fine, but those are closed or sealed, not open applications.
I used a tiny brush to apply the grease to the recessed contacts on my outdoor ClipperCreek. There is no power when not plugged into the car, but to be safe, best to open the breaker as well.
Once, when I removed the cover after a severe wind/rain storm, water came pouring out. I drilled some small holes in the cover, no problems since then.