In line air dryer/filter, not compressor. I would probably paint--you are going onto epoxy, I believe. Two part is OK--but not if it is going to be constantly immersed in water. I rolled on 2 part awl grip on the deck of my Cal 46. We sprayed the hull topsides, and the gloss of the cabin sides--we did add micro glass beads to the first coast--and second coat with no micro beads. You would get a decent finish, but not the best gloss by rolling--there are some who can come close to a spray job with tip and roll.
I would probably go with Nadicore for a cabin top (although the C dory does use balsa in the cabin top of the pilot house. Are you going to have a space between the cabin top and where you have the leading edge of the hard top? I know you live in "cold" country, but even in the PNW it is nice to be able to have some ventilation between the canvas top and the cabin top.
You can integrate awning railing so that when you want a camper canvas back enclosure, you can do very easily by adding bolt rope to the side and rear pieces, That is far better than the use of sippers.
If I was doing a mold, I would use sealed and waxed masonite for the majority of the cabin top, and then bu8ld the edges with light wood, fillets for the curve. Interesting concept of making the cockpit cover with fiberglass. The engineering of the cantilevered top is critical. Some of use tend to swing from the aluminum tubing as we board. My 42 foot trawler had a hard top over the flying bridge, of aluminum sandwich with 2" foam between. The top and edges were fiberglassed. We air conditioned the flying bridge. We rolled on a single part modified epoxy paint.
Atlantic Towers makes custom fiberglass tops, but supports them with aluminum structure.. It might be worth taking a look if you have not already.