when you say deck and hull not meeting up as it should what do you mean...some pics would help. I had some issues with my deck and hull where the previous owner bumped docks etc. I removed the rub rail and filled in the problem areas with 3M 5200....drilled out old rivets and put in new rivets glued in with 3M 5200.
Windshield gasket - easy..just have someone help you...glass very expensive.
regarding the paint...check into wrapping it with vinyl. Lot less work and aggravation and you can personalize the boat. If you have patience you can wrap it yourself....not easy...but might a good project for the winter if you have a heated work area.
...A bad day water skiing still beats a good day at work...1995 Pro Star 205....