I agree with the others that if startup costs are an issue, building from plans is the way to go. If you prefer working with wood, take a look at the Pietenpol. Its a design thats been around since 1929, and there is huge online builder support that is very friendly and helpful. It will probably end up costing at least $10000 by the time you are finished including the engine, but you can spread it out as long as you need to. I'm 5 years into building mine and doing the final assembly.
One piece of advice you'll hear over and over is to have a work place close to home. The completion rate for plans built airplanes is horrible, but if you can work on it just an hour a day and stay motivated it can be done!
Learning to fly in your own homebuilt will probably be problematic, because it has to be flown solo for either 25 or 40 hours depending on your engine/prop combination before passengers can be carried.
My advice would be to find a local EAA chapter and start hanging out with those guys and see what they are buildingm what they are flying, etc.
This website has tons of pictures of Pietenpols in various stages of completion: