Comment Check out the EAA (Score 2) 100
Having built my own plane (https://sites.google.com/site/tomscozypage/) it is something ANYONE can do. Well, not anyone, especially anyone who would rather tell us all that they can't do stuff, but anyone who is willing to spend a couple years out in their garage, basement, or whatever workshop you have getting stuff done. It is not a risky venture, if you either follow the plans, or do reasonable engineering (if you know that discipline) when designing your own.
Any avocation can be expensive. Sure you can pick up fishing for like $15 for a rod and reel at Walmart, but in a couple years, after the boat and SUV purchase, you are talking about real money. Very capable airplanes can be bought (yes factory built even) for the cost of a good used car ($15K probably for a 2 seater). Learn to fly in your own airplane, with a good instructor, and you can learn for very little.
The medical requirements are minimal, and if you are willing to stay with a 2 seater aircraft and not really high performace (Light Sport Aircraft category) you only need a drivers license as your medical certificate. Even a 3rd class medical (if you want an airplane with higher performance or carrying more than 2 passengers, you need that) can be passed by anyone who is willing to get off their butt a couple times a week and move around. (if you want to fly for money, you need a 2nd class medical, and if you want to be a captain of an airliner you'll need a 1st class medical with the whole EKG and all).
The inexpensive airplanes aren't made anymore, Steve Witman designed some wonderful inexpensive fast! airplanes (tailwind as an example). Long-eze was maybe a peak of recent plans designs, by the man, Burt Rutan. Kitplanes magazine does annual issues of various kit offerings, as well a plans designs. Wicks and Aircraft Spruce are reliable suppliers.
The EAA is a little shifty supporting the home builders, but have been the most reliable for over 50 years. The EAA chapter organization is probably the best support group in the world. Use the resourcfes available, don't do it alone. There are plenty of resources available, from tech counselors to flight advisors. Yes you can fly an airplane you built yourself, or you can have someone else fly it for you.