I've never really invested too much money in cars, mainly as my brother and I where so close he had all the hot hatches and then nicer stuff (currently running around in a TTRS), so I'd have a go in his cars and I'd buy more sensible things that didn't lose too much money where as he'd spend all his money on cars and tuning them..
Bikes feature a bit, I was fortunate that my Dad bought us a trials bike when I was very young, and no surprise I had a 125 when I was 17 (I skipped owning anything when I was 16 since I couldn't afford it!)
1977 - 1976 Yamaha TY80 (I was 6!, it was for me and my brother)
1978 - 1978 Yamaha TY175 (Brand new, shared with my brother)
1988 - 1985 Suzuki RG125 Gamma - F Reg - First vehicle, it was accident damaged (no front fairing)
1988 - 1978 Austin Mini Clubman - 1100 - S Reg (First actual 'car', total dog, the rear wheel fell off, but I loved it!)
1989 - 1989 Yamaha TZR125* - G Reg (Brand new)
1990 - 1985 Ford XR3i - B687 AGL (First hot-hatch, completely crap, got stolen then recovered, so slow it was embarassing)
1990 - 1990 Yahama DT125 (cheap example, needed loads of TLC)
1991 - 1985 Metro 1.3HL - Bxxx xxx (Stop Gap whilst saving money for a house, first time I fitted an engine myself!)
1993 - 1986 Ford Orion 1.6i Ghia - Dxxx xxxx (cheaper alternative to the XR3i for a bit more comfort and cheaper insurance, the camshaft snapped in half)
1995 - 1990 Astra GTE 16v - G781 BMO (had this for 8 years, rebuilt the engine, remapped it myself, for 156-1650BHP it was quick for it's time)
1999 - 1997 Rover 420SD - R403SDL (commuter ****)
2000 - 1999 Suzuki GSXR600 WX - T477 KAM (First actual legal street bike)* Only passed my test at this point (Direct Access)
2001 - 1998 Vauxhall Astra 1.8 Sri (The Mrs commuter ****)
2001 - 2001 Suzuki GSXR600 Y - Y67 AAM (Brand new)
2002 - 1999 Vauxhall Vectra CDX 2.0 DTI (commuter ****)
2003 - 2003 Suzuki GSXR100K3 - FY03 USC (3 months old)
2005 - 2005 Vauxhall Zafira 1.9CDTi SRi DN55 FZE (Brand new - family wagon, I'd massively hurt my back and needed something easy to get in/out and carry 2 kids etc, I still spec'd it with adaptive suspension and had the official 888 Remap to 200BHP)
2009 - 2003 Fiat Stylo Dynamic 1.9 JTD WV53 KHZ (commuter ****)
2014 - 2014 Mazda CX-5 2.2AWD Sport Nav HF14 GAX (3 months old - family wagon replacement)
2014 - 2003 VW Beetle Convertible GJ53 TVA (for the Mrs - She always wanted one, so I took the family wagon on)
[C]2015 - 2004 BMW E46 M3 Convertible (Still have this - effectively we swapped, I had the convertible, the Mrs got the Family wagon)
2015 - 2011 Mini Countryman 1.6 Cooper HK11 VLE(Smaller family wagon for the Mrs)
2017 - 2015 Nissan X-Trail 1.6D AWD Tekna (Replacement family wagon for more space)
[C]2019 - 2016 BMW X3 x35d M-Sport (Managed to win the options lottery)
[C]2021 - 2006 VW Beetle Cabriolet 1.6 Luna (Just bought it on the weekend for the daughter to learn in)
Other cars
2004 - 1999 Focus Zetec 1.6 - Ex company car bought through my brother, had it 3 months just to flip for some money and see if we preferred it over the 1.8 Astra SRi but the Mrs didn't like it
1992 - 1986 MG Metro - Bought for £50, just needed to last 3 weeks, it used about 4L of oil in those 3 weeks, then sold it to the scrapper for £40
Next Cars
Mrs - Wants another Mini Countryman, would just want a 1.5 Petrol Auto - I keep looking at the PHEV (She does lots of very short commutes, ~1.5miles) or the JCW 306 BHP, but she's now sold on decent automatics and can't blame her.. Her current X3 35d she likes, but does not need anything as quick..
Me - No idea, would like maybe a convertible 435d / 435i / 440i/ M235i / M240i but keep thinking a BMW i3 as a quirky cheap to use second car, basically I do < 2K miles per year, mainly weekends taking the family or Mrs out for a day in the Cotswolds etc.. I walk to work when I can and so any car I have is just sat on the drive most of the time!