I think the best thing you can do is just search the site. Lots of people on here have repainted their boats. I would not bother with redoing the gel coat unless it's in need of major repair (doesn't look like it).
In order to do this job right, you're going to need an area where you can word indoors and without dust. A large garage will work or, even better, a shop with a paint booth. Spraying will make it come out the best, though you could roll and tip it (but to do the deck, spraying it will be the ultimate best).
Naturally, you'll want to strip the boat of everything...
Another option is to check in with a automotive repair shop in the area. You may be able to get them to spray it (and they have all of the proper environmental and safety equipment to do the job right).
If you can't find what you're looking for here... check out
www.speedwake.com. There's a guy there that completely redid his Wellcraft (much like what you want to do) and it looks sweet!
Tom