Wow that is a lot of money for a MK4 GTI, you can have a MK5 for that sort of cash.
I would consider
MK4 $3-5k
MK5 $5-7K I found 13 on carsales in that price range.
MK4 are getting to 20 years old now.
Basically everything could be a problem. Gearboxes tend to sheer diff bolts, so you want to check for easy gear changes at high revs.
I would just look for good service history, timing belts and water pump services, suspension needs to have been redone at some stage too.
The AGU engine really did not have any issues, unless it was tuned too far or not serviced often enough. Water pumps failed early but most should have had a few replacement by now.
Check the radiator fans come on when AC is on. And that the AC is ice cold or keep walking.
Biggest issue will be age, so all vac lines and hoses could be perished and cracked etc. Interior would expect peeling plastic worn steering wheel and seats starting to wear through.
MK5 just looks for DSG issues, smooth gear changes up and down are a must.
MK4 GTI - Sold
MK5 Jetta Turbo - Sold
MK5 Jetta 2.Slow - Until it dies.
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