Just yesterday I scraped a skeg against the roller mount as I was pulling her onto the trailer. This has happened before.
|Scraped the skeg on the trailer rollers|
I've had to do more maintenance on the skegs than on any other part of the boat.
If I had to do the skegs all over again, I'd seriously consider just building the things out of 2" UHMW plastic. I have no idea how to bond UHMW to the hull though. I expect that even bedding compound won't stick to UHMW.
There are roller guide end caps that should protect the skegs. I'll do some investigation.