Peugeot 309
I bought this at age 15 for the great sum of 500 DKK (~67EUR, ~52GBP, ~84USD). I think this was with 1.1 L engine so not much power but it didn't really mater since the car was for trashing round on a empty field until the fan belt jumped off and then fix it and repeat. Also despite being made of the thinnest metal known to man it was remarkably rust free. I the end I used it for a school project when the engine had long seized up from standing around.
Nissan Sunny (Pulsar, N13) 1.4 LX 12 valve
This is what I consider my "real" (read roadcar) first car, my grandfather gave it to me when he stopped driving at age 80, I was 16 at the time so the car stood for 2 years patiently waited for me to turn 18 (minimum driving age in Denmark). When I turn 18 we pulled it out of the shed it been sleeping in and after a normal service, a rear brake cylinder ,some new fuel lines and a pair of front wings it was ready to drive it even went through the MOT with out any problems. Although the rust from standing around plus now driving it about 100 km each day meant the exhaust didn't last long. So I installed a new rear muffler and that was about the last I did too it, just drove it for the next 2 years. It never missed a beat, it did however make increasingly weird bumps/rattles/other strange sounds.
Ford Capri 1.6 L
At age 19 I felt that I wanted a project car to work on and while through various cars I started to really want and old Ford, either a MK1/2 Escort or a Capri but I ended with wanting a Capri slightly more. One problem though, there where no cheap Capri in semi-decent shape for sale in Denmark at the time. So I expanded my search and found one down in Germany. It wasn't really in great shape but as I wanted something to work on rather than a driver, I thought it was okay. On the way home the carb also showed that it had some issues, mainly that sometimes (most of the way home in fact) it would not keep a steady speed, it could slow down every slowly or accelerate, no middle ground at all. Another issue was that even in summer it didn't always want to start when it was cold without some starter fluid. After driving around on the temp. plates I got when I bought the car in Germany, I parked it in the workshop, bolted off the rear axle and started to work on the bodywork, until that I was told that I needed to make space for some rebuilding. So we moved the car out of the workshop with a makeshift rear axle and I haven't got back to it..
Peugeot 405 T16
About half a year after I bought the Capri, one day while looking at my normal places on the internet, I wondered what I 205 T16 goes for, turns out they are expensive (as expected), I first looked at the German sites because it unlikely there was one in Denmark, but just for fun I searched anyway, and there was a 405 T16 which at that point I was only aware of the Pikes peak and Dakar version which are basically stretched versions of the 205 T16. And since I had been watch all the group B documentaries I could get my hands on, I was intrigued by this unknown car with a T16 badge. Of course I started reading up on it and the stats read very similar to the great rally homologation cars of the time. 2.0 L I4 with a variable turbo developing 200 hp or with the overboost 220 hp, full time AWD with a viscous lock in the center and a Torsen diff at the rear and Citroën based self-adjusting hydraulic rear suspension. Obviously I ended up buying it, It's a great car especially in the winter because it will oversteer when you want it, but when you don't you just change into a higher gear and it becomes a comfortable and stable cruiser. The bad sides: being a rare car, parts can be a bit of a pain and well it's not exactly economical.
BMW 320i (e30)
After dealing with Peugeot T16 parts, I only had two requirements for my next car 1: good parts availability and since I had a FWD and AWD daily drive clear it was time for something with rear wheel drive. Also my budget was small... very small. So the list quickly narrowed down to, Sierras, e30, e34 and 70s Opels, another possiblity would have been Volvo 240 but I tried one and it's a bit of a boat, could just have been a bad example though. The Opels where too old for a daily drive on the cheap (rust), I was never a fan of e34s even though it's most comfortable and the newest car in the list and funnily the price doesn't reflect that. I the end I just wanted an e30 more than a Sierra, so I searched for a bit and fund one that looked to be mostly rust free for cheap-ish. In the years I had it, the fuel tank rusted threw, a cambelt snapped (I never got round to changing it) and I did end up making fair bit of various rust repairs.
Toyota MR2 (AW11)
This time round my requirements where extremely vague, either I wanted something both dirt cheap to run and buy or I wanted something interesting where I wouldn't mind spending a bit more money. While talking with the other IRC regulars, our resident Toyota fanboy (adam_d) mentioned that he wasn't going to suggest any Toyota since I had expressed my dislike with any newer Toyota except the Toybaru. So I looked up the few Toyota I do like and found a good example of my favourite gen MR2 that was close to where I work. This car definitely have mid-engined handling characteristics, it's also eager and quite economical for 25 year old car. I have driven 20 Mm (that's Megametres) in it and the only problem I had was when a marten had bitten in the HT-leads
TL:DR
Daily drives: Nissan Sunny -> Peugeot 405 T16 -> BMW 320i (e30) -> Toyota MR2 (AW11)
Others: Peugeot 309, Ford Capri