GM all of the above. I sprayed the outside of the bow to the windsheild, then sprayed the recessed area and the top / front of the windshield frame from inside. then sprayed down the outside about 8' towards the stern. Then got back in and sprayed the inside of the gunnels and around the dog house. Then back outside to finish up things. I go from one side to the other to keep a wet edge as I am going. Good workout!
As for wood, I picked up some s4s maple yesterday for $3 BF. The Sapele was $5.50 BF in the rough and I got a quote for s4s quarter sawn white oak at $6.50 BF. All 4/4. I bought small quantities, usually it gets cheaper once I pick up more than 100 BF.
I always ended up sanding through the primer on corners We used to spot prime stuff all the time when I worked in the body shop. If it didn't need body work, we just sanded down the paint and went to the booth. I usually spray a sealer (which was a pain in the butt this time) and let it tack up. Then come right back with my paint. The sealer takes care of any transparency splotches in the paint. That usually isn't an issue with solid colors other than reds. Metalics are a whole other ball game, the color under them can really change how they look. As far as adhesion, never had an issue fiberglass as long as it is sanded and clean.
Pat I have no idea on the tip size of this gun, other than it is "correct" lol. By that I mean it is a good size for the speed I like to work at. I will try to take a look later. It could be slightly bigger, but works fine. I'm currently using a DeVelibiss Finishline gun. Not quite a Sharpe, but still works pretty good on metallics. I have also seen some good paint jobs with cheap guns too. Solid colors are a lot more forgiving, metalics really need a good gun.
As for pressure, lol again I have no idea! I painted so much in the body shop that you more or less listen to how it sounds and look at the pattern, I would guess around 45 or 50. I use a regulator on the gun right before the screw on water filter. (the filters are great by the way, get one) I would get a regulator with a gauge on it. I like that because you don't have to fiddle with the regulator on your compressor. I usually open up the air on the gun, get it to where it sounds right, then squirt some paint. You want a nice even fan. If you don't have it high enough, your pattern will be too wet in the middle. Too much and it will be dry in the middle and wet on the outsides. I'd see what Nason recommends on pressure and start in the middle (they probably have a recommendation on the tip too). Depending on your gun you will need to fiddle with it a bit. I usually keep the fan almost wide open, and only tighten up the pattern when I cant get to something. It gets really water gun like when you tighten it up. The trailer should be good practice, I leaned painting semi truck frames. Start at one end and work your way to the other!