Steve, I think I've got you covered on this item.
I dropped the CB on my 95 H26 this spring for repairs. My boats bottom (it sounded too kinky saying "my bottom") had a factory authorized blister repair that included epoxy and paint. They only painted the part of the CB that hung down with the boat on slings. The CB trunk housing forward of the aft edge of the hanging CB can not be painted without removing the CB and its mounting saddle. The aft 4 1/2' of the trunk, with the CB hanging, can be painted. If you use care when launching your boat and if your dock crew does'nt pull her off the trailer then she should just float and not damage the paint at all. Additionally, I was concerned about the condition of my factory installed CB raising and lowering line. Was she frayed, streched, brittle or otherwise bunged up after 7 years of use? We had only had her for 1 year but raised the CB probably 50 times. Since I had the CB out I replaced the line. The original was in perfect condition!!! No need to worry. Go forth, paint, sail and enjoy!RayS/V Speedy