Head gasket failed!! - this had recently been changed before I bought the car, but was an amateur job. The head bolts should (apparently) only be used once - mine had been reused so did not stay tight.
Several burst radiator hoses shortly after head gasket work.
Radiator fan thermostat failure.
Suspension cannot handle pot-holes anymore - not sure if this is suspension or shockers or both, but the effect makes the cd player jump and the driver/passenger to check for any minor bone fractures.
Stiff clutch (anticipating imminent failure!)
This might sound like a nightmare, but the first thing worth pointing out is that in spite of some demanding driving this car has never failed to get me where I am trying to go (touching wood I am!). in spite of overheating, gasket blowing, hoses splitting, this car has yet to get to the point where it refuses to move on me.
I did have a glut of problems soon after buying it, but since I have got these fixed up the car has been a model of convenience and reliability. I also give this car decent marks because the repairs have all worked out to be pretty cheap, and parts availability has not been an issue.
The problem with the ride (mentioned above) is the only persistent problem - I have never really addressed it properly since on decent roads it is fine. Minimal roll round corners and, though you can feel every bump, a relatively comfortable ride... until you hit a pothole... the shock travels right through the steering and is delivered powerfully to the driver - everything is jolted and the experience is quite alarming (If any other golf/scirocco driver knows anything about this please let me know to email@example.com)
The scirocco has a capacious boot, and though I am 6ft 1 I have no problem with the roof height (in fact I far prefer to be 'close to the road' than in a 'sit-up-and-beg' position). Back seats fold down to make this car a very practical carrier for minor house moves, bicycle transport and so on.
Fun driving, though no stunning performance off the line - I have taken this 15 yr old well-used car upto 125 mph yet at comfortable 75 mph cruising she still manages a comfortable 40-42 miles per gallon.
I spent £500 odd on the car, and about £500 on repairs and new tyres etc since. All in all I have got 15k good miles out of it and anticipate a good few more (as long as the clutch holds out).
When the clutch goes I will have another decision as to whether it's worth the repair, but with the body in mint condition, and a flourishing relationship between me and the car I think it might well be...