Skidmark,
For the damage you're talking about, I would use FeatherFill or a similar product. It's a sprayable polyester filler similar in composition to Bondo, but you would not be likely to have the moisture penetration/lifting problem described above. Also, since fiberglass is also made from polyester resin like Bondo and FeatherFill, it should adhere well provided the surface is clean and grease free. Be sure and clean your gun THOROUGHLY after you finish spraying it; if it sets up in there...well, your paint gun will make a good paperweight.
A side note here for ANYONE planning to paint your car: avoid silicone lubricants like the plague. It's a royal pain to get rid of, it gets everywhere, from just a tiny spray, and virtually no paint will stick to it. (Unless you just like the fisheye effect.) Most body shops will not even allow them on the premises.
You might also do some research on boat repair; gelcoat on those has gotta be fixed from time to time too, and it isn't a nuclear secret or anything...
Tony
[This message has been edited by Vonov (edited 05-08-2004).]