I learnt to drive in 1996, and 3 weeks later binned my mum's Audi 80 into a bridge parapet and a telegraph pole.
Spent a while then with the only vehicle I regularly drove being a massive VW LT-wagon, which teaches you a bit about road positioning, and taking account of width and wheelbase!
For my own cars, I have had:
Vauxhall Astravan - absolute shed, should have already been in a scrapyard when I bought it, and went to one a year later despite having had the engine, radiator, two doors, fuel tank, and several others parts replaced.
Volvo 440 - Terrible car for an 18 year old to drive in theory. But in fact, same price to buy and insure as an Astra which was so much worse a car in every way, it's not even funny.
Mitsubishi Colt GTi-16v - Did eventually decide the Volvo image wasn't great, and went for a boy racer hot hatch.
Alfa 145 Cloverleaf - Still hot hatch, but a bit classier and a bit rarer. Never made a conscious decision, but I don't seem to have been able to move away from Italian cars since I bought this in about 2002.
Fiat Coupe 20VT - Stonking car.
Alfa 156 GTA sportwagon - Still got this, owned for nearly 7 years. It's an excellent mix of practicality (albeit not in terms of running costs), looks, sound and pace. Hard to see me changing it any time soon either. To find anything with similar qualities to replace it, I'd have to pay about 3 times the cost.
I would say that, throughout my driving life, I've always been able to look back and think "Christ, I was nowhere near as good a driver then as I thought I was."
There's no reason to believe that the same won't be true in another 2 years looking back to now. So it's good to recognise that you've improved, just don't ever think you've reached the end of that road!