In the water is where a boat belongs. Congrats! Interesting about that lock pin hole. After I suggested where it might be I was looking at your pics again and thought that I saw your drill just finishing the job on the trunk. Guess not.
I have to believe that either 1. your wire is too short(that would be easy). 2. Something is jammed up in the trunk(no big deal). Or you have the pivot bolt in the wrong spot(Yuk!)
Didn't get out much when daughter was here, but last night went out with 20+ gusts and learned a bit more. I had the smaller of my two foresails on, but still too much. When I dropped it, not easy in those conditions when solo, the main did just fine. Must confess that I forgot about the roller boom or i might have tried it. I wonder how you lock it in once rolled
Have decided that I need roller furling/reefing for the jib, or at least run the halyards back to the cockpit and put a downhaul on the jib.