Will you convert to a retaining "snail" pin to hold the rudders on the pintles?

Don't worry, it's all experience. I bought an old mosquito and broke something serious almost every month. Until now the only original items left on the boat is the tramp (which was been re-stitched), boom and the port hull! First it was the sails, then rudder blades, then the rudder boxes, then the mast, then the beams and I'm now building new hulls (F16) after breaking the stbd hull in half.

It is very frustrating constantly building/repairing a boat. I'm sticking with it because it is a challenge which I will learn a lot from, and everyone needs a hobby.

Two hours to rig seems a bit much. Have you checked out the other cats in your area?

Maybe see if you can get a crew with someone else for awhile, get the boating bug back and learn from them. A different perspective can often be very useful.