I've always dreamed of buying my own plane. Turns out, they can be had for $20,000 on eBay. This sounds too good to be true.
What checklist of items are essential to prevent my new purchase from falling out of the sky?
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There are plenty of great $20,000 aircraft out there - the hard part is finding them.
"What to look for" is an incredibly broad question, and varies substantially between different types of aircraft: You would not look for the same things on a Piper Comanche as you would on a Cessna 182.
Accordingly the first thing you want to do is find a mechanic who is an expert in the particular type of aircraft to help you check it out and do a "pre-purchase inspection".
Finding those mechanics is actually pretty easy: Look for a "type club" that supports the aircraft you're considering and ask them for recommendations (e.g. for a Cessna I'd talk to the Cessna Pilot's Association, for a Cirrus COPA, for most Piper aircraft the Piper forum, for Beechcraft Beech Talk, etc.
Talk to folks on those forums (and to your mechanic) about what you, as a buyer, should be looking at before you get the mechanic involved for the more detailed inspection. There are lots of things you as a pilot (even a student pilot) can determine just by looking at a plane (and/or the logbooks).
Some key items to look at before you go see the plane:
If all that looks good it's time to look at the plane:
If the aircraft passes all your checks it's time to turn your mechanic loose on it - they will inspect the aircraft for problems (major and minor) that you as a pilot might not notice which can wind up costing you a lot of money. This pre-purchase inspection (and the ensuing negotiation based on what the mechanic finds) is usually the last stop before handing over your money and taking the keys.
Well, this is a much more opinion based answer, but I'll give it a go:
After that, I would say getting an independent inspection by a General Aviation mechanic, and go for a test flight with the current owner (hopefully they will be willing to fly in the aircraft).
Hope that helps.