It's great to start a new topic to ask a specific question like this, but please include enough information for people to give an answer, don't assume we know what kind of boat you are talking about. Not everyone reads every topic.
And as MN3 said, pictures help a lot. For instance I'm not sure what you mean by "rudder bolts" in this context.
Sorry for confusion and haven't figured out how to insert photos yet. I have a Prindle 18 and noticed gel coat is chipping away where bolts that hold the rudders to the castings patrude through. It looks like the bolt head should possibly be inside and the nut on the outside providing a bit more clearance.
Common thing in Prindle 16 & 18. Occurs when noobies throw the helm over too much when tacking. Happened during previous owners time with boat. Just fill small dents with silicone or epoxy/microballoon mix & sail the boat. Pete
Go to user photo albums and create one for yourself
upload images there - then right click on them and "copy image address"
now back at the thread you can click on the IMAGE button below and paste the image address between the IMG tags
Trailering with your rudders on will worm out your fittings/ holes, and add slop to your rudders (slow)
every bump you hit in the road, will make your boat slower (kinda kidding but there is some truth to that)
If you drive more than a few miles, or drive on bumpy roads you should remove your rudders, it will: extend the life of your gear, reduce slop in your steering system and .... Sail faster :)