-Buy used october through december if you can. The prices will be lowest.
-Buying a "project boat" isn't necessarily the worst thing if you are handy. Yes it's nice to have some experience repairing before you drop alot on a boat but some boats go REALLY cheap and only need a few days of work. I just bought one of those for $50 and this boat will make it into regular rotation. If it wasn't gonna make rotation I would just sell it for a few hundred dollars.
-If the patch has a buncha glue under it, beading around the edges, or squished out from the edges or generally messy, it was probably done by a newbie and may not be the best patch.
-I may *kinda* disagree on not buying boats from outfitters...it really depends. Private boaters typically want more for their rig and try to suqeeze as much as they can out of it. Outfitters typically can give you great deals, but quality will vary. I see outfitter's Hysides from the Ocoee for $500...the boats hold air well but are heavily worn, maybe torn handles etc. I have one 15 year old Star used by a fishing guide on the SoHo and Watauga and it lookes great...I also have a 31 year old Hyside that was owned by Ace and guided paddle groups down the New and Gauley river for years. I also have a 4 year old NRS that was a practically new demo when a guide backed a trailer into it....was patched by the warranty shop and sold at 1/3rd the price. The point is be patient and look in the right places and you will find great deals.
I hate to be this way because it's a little predatory, but keep an eye out for people who maybe frustrated with their boat , who are moving, getting divorced, getting older (hence coming towards the end of their paddling career) or make friends with a repair shop and buy demo boats. If you see someone with newly a punctured tube...go talk to them, it's crazy to me how quick people are to get rid of boats that just need a little repair and or elbow grease. Maybe they can't get the floor stiff....well often it's just a dirty prv that needs washed (I've bought one of those)...or the floor needs reglued, or a slow leak needs stopped. People are lazy, so capitalize on that. I've bought boats from people in most of those ^^^ categories.
Now I have a reputation as "the guy who will take your boat", so that helps