I suggest checking the posts and forums at oldhouseweb.com. Many other old home owners have gone through what you are facing and have posted their experiences.

Good luck and hope you get rid of the vinyl!

I didn't do it yet with my house, but I did look into what we need to do. Taking vinyl siding off is easy, I've done it by myself, then make sure all the nails are out. Fill in the nail holes with putty and sand flush. Now the hard part, you will probably have to come up with some window trim and corner boards or whatever woodwork was stripped when your house was prepped for vinyl. Depending on if and how your windows were replaced you may need to get some siding too or you may need to reinstall the windows now that you don't have the same wall depth. Then prep for paint (scrape, sand or strip old loose paint), prime if needed and repaint.

I can't imagine any risks involved, but again I haven't actually done it yet.