Let me be your Jedi master friend. I am 24, living on my first sailboat which I bought as a project, and am also pretty poor, monetarily speaking. First off, for the money your talking the boat you buy should be pretty much ready to go. Im serious. This is a buyers market and for $6,000 you should be able to find a 26-28' boat that is well equipped and for the most part ready to go say for minor things and cosmetics.
Or, you can do what I did.
You can spend $2900 on a boat you find off craigslist and you can buy that boat and realize you now have to rebuild practically the whole thing--- Having completed 2/3 of the entire process let me tell you that I have far exceeded $6,000.
So, you want to know my best piece of advice? Seriously?
Know what your looking at. Then, once you know, figure out if its in working condition. Lastly, if it is not, figure out how much it will cost to make it that way.
Now add up all of those costs and decide if the boat your looking at is worth it.
Look man, I've got ox will power too but I can say in a second that if I could go back knowing now what I didn't then I would have waited on a boat that was in better shape and required much less in renovations.
Here, please friend don't take my advice alone. I have done a shabby job of taking pictures of the entire process. I have left out a hundred or more pics of things I just neglected to take pictures of but here is my photobucket account. Please look through it, it has a lot of things you will find in the at your price range-- Such as what old sea cocks look like, bad wiring, corroded mast, bad standing rigging, before and after shots yadda yadda- good resource for a guy with your level of experience and depth of pocket.
Pictures by trisstanseth - Photobucket
You do not need classes. Understand your points of sail and sail trim and READ. READ lots. This and other websites are great and I learned a lot from them but the value of a Chapman or American Practical Navigator is not to be underestimated. Read stories of when things go wrong- That way if something similar should happen to you hopefully you will be able to get yourself out of the sticky situation.
Had I not read Voyaging Under Sail I probably would not have been so quick to alternate my tack after losing a chain plate in 20 knots, nor would I had probably been so quick to think to run my Jib line through the turnbuckles and then winch the line under the toe rail to support the mast.
So, read, read, and read some more. Also, go to your marina and look for the guys working on their boats. Ask questions, ask to look around. If you see something you don't know ask. This goes back to point one.
Point in case- I saw when I looked at my boat that the bottom 4" of my keel stepped mast was corroded. What I didn't realize at the time was that corrosion was a structural deficiency that would require me to take the entire mast out of my boat (haul out fees), chop off the corroded portion, re sheathe it (welding fees), and drop it back in. Whoops- Did not know what bad standing rigging looked like- mine looked good until you see the hairline cracks or the one or two strands of broke stainless thread sticking out signifying the need for an entire new rig set- up ($1500.00).
Do you know what a weathered main looks like? Can you tel if your sails are in good condition? I thought mine looked fine- did not know what UV damage looked like. First time I raised it in 20 knots it ripped the entire main. New main = $900.00
Does the electrical equipment work? That stuff gets pricey fast-- Since I am young and poor I bare bones it. No AC, no refrigeration. I have three cabin fans, 4 cabin lights, some gauges and meters and a solar panel with inverter for running my laptop and cell phone charger. The cost of setting that up? $1200.00.
Will your boat need a haul out? $150.00. Does it need to be painted on the bottom? First lets hope no barnacles have eaten through the gelcoat. $$$.
See, I can go on and on and on but it all comes down to knowing what to look for. See, I thought I had a good idea but NOW I KNOW. I know every nut and bolt of this boat and I still have issues (run away diesel at times, head sink pump not working, ice box doesn't self drain, main still shredded, cabin portholes needed, line, rode, EPIRB, not to mention a passport to even go somewhere.
Heres what I would do. I would either get a friend who KNOWS boats to go with you when shopping.
Or, I would pay a surveyor to survey any boat you were serious about buying.
Last, I would PM me or someone else here and ask very detailed questions with pics included if possible so I or someone else here can help you avoid making the same mistakes I, and I am sure others, have.