Hi Jason. Welcome aboard!
I built a Short Shot during the winter of 2016. At the moment, I don't have time to say a lot, so I'll respond with some quick answers and maybe others can chime in too.
1. Buying the kit will not exempt you from 'wood working'. But the wood is soft and easy to cut. Also, it's a simple frame to be covered, not a grandfather clock on display so it doesn't have to look perfect.
2. I paddle on the Hudson River too, but up around Albany/Troy so I don't see a lot of waves. You should be fine though if you're experienced in those conditions. I recently paddled several yards from the edge of a calm lake and jumped in the water just to see if I could get back in. I did no problem.
3. I'm a little taller than you and about 20 lbs heavier, but I don't carry much on board with me. She tracks just fine.
4. Your size 9's should fit just fine.
5. I don't have a spray skirt and I haven't rolled my Short Shot. Someone else will have to answer that one.
Good luck!
- Ben