John, the world has changed. The assumption and popularity of cove and bead strips has come to a halt. Very few builders are doing that. its an enormous amount of extra work and not necessary. C & B is nice for canoes where the complex bends don't exist.

No money saving with a painted hull. Once you do a strip hull, you'll be amazed at the beauty of the wood no matter what you use. Its pretty hard to do a terrible job because the method of putting down strips one at the time forces you to get very acceptable fits. Don't assume you will need 10 gallons of filler. I'll bet you need almost none.

Try to enjoy the process but others can chime in - but cove and bead is almost never used any more on kayaks.

Wide strips are fine. I have a pretty flat back deck on my boat and I've used 5/4 wood there. (mostly because I had that stock). Once you do a few strips, you'll get pretty good at it - everyone does.