Here's what I've run since I was sixteen.
I originally bought this '84 Vanagon that I have discussed before. Subaru 2.2 swap, four-speed manual. Learned how to drive manual in it as well. Bought it spring 2006, drove it on learner's permit over the summer of 2006. Got my license fall 2006 and drove it up until the winter. Due to a variety of reasons (eg, potential rust issues that I wanted to prevent, no heat, etc) I put it away for winters, which meant a few years of procuring $300 beaters to get me around during the winter months.
Boston - parked next to an example of a car I would eventually own, but never would have guessed at the time.
Note how it's parked across a regular space. It still fit.
During this time, I also ran this '70 Subaru 360. 25hp two-stroke twin mounted at the rear. Suicide doors. Dog-leg four-speed with non-syncro first gear. It was quite the fun ride, if slow. Unfortunately and unsurprisingly, money became tight and I had to let it go. It's in a museum in Massachusetts now.
One of these cars is American. The other is not. Can you guess which one?
My first winter beater was this 1993 Ford Taurus. Hey, it did get me around. Unfortunately, like all Tauri second-generation and beyond, it was an automatic. At least it kept my van out of the salt. Bought for $400 and sold for $600 in the spring.
Ran the van for spring, summer and fall 2007, purchasing this beat to shit '93 323 (also an auto, unfortunately) for $300. That was the most horribly beaten car I have ever owned, but it ran and ran. Sold for $500 in spring of 2008.
Ran the van spring, summer and fall again. Bought this '94 Excel for $700. Five speed. Unfortunately it did not last a month as the oil pump failed at 66,000 miles (carfax legit miles), so I did not make out so well. Sold the rest of the car for $350.
Bought this Prelude for $700. It got me through the winter, however it was dual carb'd and therefore it was a real bitch to start. That, and the right front brake was nonfunctional and therefore the car went into a slide every time I hit the brakes on a loose surface. Five-speed. Taught me a serious lesson in car control. Sold for $500 in the spring because it wound up having some more issues that I had no time to deal with.
The van was sidelined for the spring and it currently awaits a restoration once I have the time and expertise.
At that time, I had a pretty good amount of money saved up so I bought this five-speed '92 SL1 for $1200. I did a bit of work to it and it got me around for a good 12,000 miles or so before problems became too severe. Sold for $750 - a decent return on a car notorious for not holding its' value.
At this point I could finally afford full-coverage insurance so I bought myself a six-speed '08 Versa SL. I'm keeping it stock so it will be a nice reliable daily driver while I restore the Vanagon.
My dad and I also went halves on this '88 Mercedes-Benz 420 SEL that - so far - has been a REALLY sound investment.