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MagicRide said..segler said..
I need to try to answer MagicRide's question. For the 35-odd years I have been windsurfing then windfoiling, I have always pushed a fin or foil into the finbox. If it was deep tuttle, I rocked it fore and aft a couple times to get it seated, or nearly seated.
Then I take the first screw, push it into the hole, jiggle it around gently until it finds the threaded hole, then spin it with my fingers a good couple-three turns. Same thing for the second screw. If things are lined up, and the threads are clean/not damaged, this finger turning is very easy.
Only then do I grab my screwdriver or nutdriver and tighten the screws on down--by hand. Never with a power tool.
MagicRide said: "All the other bolts on the kit can be started by hand but not the tuttle bolts that connect tuttle head to board."
If that is true, then there is something wrong with alignment or thread damage or cleanliness or something. If you can't start the screws with your fingers, something is wrong. You have to find and fix that problem. If you have to use a tool to start the spinning, you are asking for trouble in the form of cross-threading.
Yep, I used the Allen wrench tool to start the spinning only on those tuttle bolts connecting foil to board because I couldn't get my fingers inside the hole to hand thread first. I will try again and see if my fingers can get in their to spin the bolts again, but it seemed pretty tight the first time to move my fingers around in that hole. This may sound stupid, but maybe there's a technique to this I will figure out.
Yes, in your defense, those screw tunnels are a PITA for that reason. You are pretty much obligated to start them with something that reaches all the way in. If you must use a tool, as I suggested, using a very light grip/fingers etc should give you a better feel if those first few turns are easy or you are cutting metal. Again, pretend you are cracking a safe on those first few turns and that you should be able to feel everything. When you turn the screw backwards at first, you should be able to feel the threads fall into place and you can begin rotating in the correct direction. If you can't feel that "drop in", that's an indication that things aren't in line.
If you have something smaller in diameter, say a smaller phillips screw driver, dowel, rod, etc that's just small enough to fit down the threaded hole without engaging the threads, you can use that to help see if the alignment is good.
If you think this is fun, imagine having barrel nuts that are a touch too loose and spin around if you hit them slightly off center with your screw. It takes about 10 minutes of: "no that's not right"/remove foil/reinsert foil/try again. A problem solved by a touch of silicon on the edge of the nut so when you get it right, it sets in place.

IT DOES GET BETTER! That's why we are all here for you. Good luck.
btw, to their credit SS have always taken care of my friends when there's a problem.