For boats...demo, demo, demo. Any shop hand worth their neoprene will be able to suggest some things for you to try out, but every boat has its own "personality" for lack of a better word. While you're figuring out the boat you like, you can begin to accumulate gear. Paddles, skirts etc. can all be found pretty cheap used. I recommend purchashing any safety gear (PFD, helmet, throw rope...) new so you can be sure of its history. Roll classes like those from Renaissance Adventure Guides or through local clubs will set you up with the skills and buddies you need to get into it. I learned to boat pretty much exclusively from my paddling club and buddies back home. Most of the buzzards will give good advice if you have any questions. Good luck and see ya on the river!
2510 47th St #A1, Boulder