When I was 16 I bought a non-running 1967 Beetle. It had dropped a valve, and with some guidance from the husband of one of my mom's friends and a Chilton's manual, I got it running. It was so noisy until things got broken in that when I went to a drive-up window to order fast food, I had to shut it off so that they could hear me order! But it ran, and I had my own car - I was king of the world!
48 years later I recently replaced the head gasket on my step-son's 2009 Corolla. I hated just about every minute of it, but it runs perfectly and there are no leaks! It also save $3400 by not paying to have it fixed.
When I was about 18, I bought a 66 Bonneville. Still have it. I wanted to put better heads on the 389 - both for a bit of flow, and to lower the "muscle car" compression down to cheap gas. I bought a pair of 6x heads from a guy in Ontario, brought them back to PA, had them surfaced, and I installed them one afternoon. The next day I drove it to FL for spring break. I stopped a few times to get the valve adjustment just right, but it made the trip beautifully.
Oh wow, I just remembered my ACTUAL first big project. Trying to remember if I've shared this before.
I bought a 4cyl Monza with a rod knock from a friend for cheap the summer after HS. I was working at an oil change place and the owner was happy to let us wrench after hours. His opinion was that I should drop the pan, change rod bearings, and see what happens. MY opinion was that I should swap in a 305 and I somehow hooked up with someone who had crashed an original V8 Monza and kept all the parts needed for a swap.
Someone had a 305 in a Firebird he was replacing, so he drove it to the shop ("Lube It All") and we pulled his engine in the parking lot. He took his nice M/T valve covers but a mechanic next door sold me a pair for $10 that he must have pulled out of a landfill - when I tried to clean them up with a wire wheel, I started putting holes in them.
I spent the whole summer cobbling it together after hours. I actually took a few (illegal) drives with it. Upset the neighbors (long chat with a local cop about that one). Sold it at a loss at the end of the summer.
My first big project was in the mid 70's was converting a '66 Mustang with 200 cid in line 6 with a three speed and really bad 4 lug brakes to a built up V-8, 4 speed toploader, 5 lug brakes w/ rear end from a V-8.
Also added GT350 springs and shocks. Quite a learning experience. I assembled the engine, rebuilt the transmission, Holley 4 barrel, headers, Edelbrock hi-rise, 11:1 pistons, better cam.