I learned to drive quite late in life, only when I needed to for work.
Short list:
1997 Pontiac Sunfire - The beater my dad kept around for me in case I eventually wanted to drive, else he was going to sell it to charity for a $75 tax receipt. After 6 months driving it got backed into at walking speed 3 times (back up, crunch, pull forward, back up, crunch, pull forward, back up, crunch, pull forward) in a parking lot, even though the last two times I laid on the horn and yelled at her to stop, by a woman who "thought she was only climbing over a curb" (note: also not how you back out of a parking spot, but I digress). A small scratch across 2 panels means a paintjob, which wrote that POS off for what started at $425 and ended up at $1575 after some shrewd negotiation.
1998 GMC Safari - The day after I ended up on a goat farm in a thunderstorm trying to buy a van from a man from Afghanistan who didn't own the van but did think Hitler would rise from the dead and I think was trying to just use the charade of a van for sale to have me transport a dead goat and a gas can back to town, a friend insisted I stop risking my life following dubious car ads and just go down to the auction he worked at and buy a van. So I did, this one, for $650. Served as a work van for a summer, (spent $1400 fixing steering, paid a shop, just needed it done), never drove it again. Idiot thieves broke the lock trying to pick it (it was unlocked), and scratched it in the process, failed to take anything, and wrote it off. If it wasn't still being used as a convenient box to store junk I've been too lazy to get rid of, I'd have finished filing the insurance paperwork. Looks like I'll get $2500 for it.
2000 Dodge Caravan - Used the $1575 from the Sunfire writeoff to buy this. Great vehicle, and great vehicle to learn to wrench on since there's a dozen at every junkyard. Wreck a part? Move on down. Wreck that one too? Move on down. Oh, that's how you get it out. Hit a deer with it and rebuilt lots of it. Later, doesn't really count, I bought a 1997 Caravan temporarily for someone else, fixed it up thinking "at least knowledge here applies to 2 vehicles", and then sold it to them once it passed safety. Awful idea, soon as you touch a friend's vehicle, you become the mechanic of it until it's melted back for scrap. Still driving it, (the 2000, but the '97 has also yet to die), it's decent and functional.
1985 Honda Nighthawk 750CB - I wanted to built an electric motorbike. My requirements were "a" motorbike, cheap. I know nothing of bikes. A friend said "You can pay less than $500, but you'll end up spending more than $500 to get a $500 bike if you do". Someone found me a guy parting this one out. He'd botched the engine rebuild. He wanted $8 for the rolling frame, and $1 for each major part. I don't know how many major parts there are in a motorbike, so I asked for all of it. He said it was in pieces. I said that's okay. He said, well, would $20 be too high? It was not too high. I picked up a frame, and trash bags of parts and unsorted hardware. Took me a couple weeks to figure out what things were, and start making educated guesses as to what bolts went where based on number and length. Got it wrong lots. Got it 90% finished and then it's sat since, as my free battery source dried up and I wanted to make sure I had enough batteries for an electric car. I've never ridden it.
2009 GMC Envoy - Was a friend's, given to them, out of province, and needed one major thing fixed before it could be safetied. I offered to help them (not do it for them, help them) fix it any time they ever wanted to, but they let it sit for 2 years, then just decided to get rid of it at auction. I suggested that was foolish, as, without in-province paperwork, all buyers would presume it had problems so large as to not be worth fixing. Auctioneer friend agreed, said it would fetch $700 max. Friend said okay. I said you're not actually going to turn a $7000 car (a gift, at that) into a $700 one because you don't want to swap one part, are you? Yep, just wanted it gone. So I saved them a trip to the auction and paid them $700 on the spot. It was supposed to be a quick flip. I did the work on it immediately, took me 3 days to do a 3 hour job, but, I got it done. Instead of flipping I noticed.. when you drive a shitty vehicle... you have to own two shitty vehicles. So when the Caravan misbehaves, the Envoy keeps getting driven until I feel like investigating. So, I still drive it, defeating the purpose of a flip. I did intend for the flip to fund "fun money" to build what became my GT.
1970 GT & 1972(?) GT - Came across the forums here after buying winter tires for the Envoy and spotting a GT (sold) in their lot. SLRacer hooked me up with a seller handling an estate in Phoenix with 3 GTs he wanted gone. Him and GTRoy drove over to look at them. Mike bought one, I bought the other two for $200 apiece, plus $200 for a pair of newly upholstered seats and $100 for boxes of "misc" (a full interior kit, among other stuff). So, $700 total for the 2 cars. The catch, I only have room for 1, I can only tow 1, and the estate could only find papers for one. Doug and Mike helped move them to Doug's ranch, and Doug started tearing them apart for me until I could find time to drive down. 3 days with a grinder performing some surgical precision, 3 very favorable inspections (2 in a thunderstorm from 300 feet away), and one car was legally mine back in Canada.
A 6'x16' trailer, if that counts - Doug had left one GT on his trailer, and had been trying to sell said trailer to his neighbor for $500. Neighbor was flakey. I needed to rent a trailer to get my GT home, it would've cost me $500. I bought Doug's trailer. Then I sold it to another local Opeler for $1, who stores it and will let me borrow it anytime, or, buy it back if I pay him back for whatever he had to fix on it in the meantime (tires and deck, probably).
I think that's all, but I've only been driving 5 years.