I love this car. It's fully loaded and the quattro is amazing in the winter (you know this)
At 208k miles my baby has been around and needs a couple gaskets replaced, along with the timing belt. Repairs are about 1400$. The KBB of the car is about $3300.
Should I even bother fixing it up or should I just drive it until it's done??
I love this car but I'd hate to spend 1400$ on it, just to have another 1400$ of repairs in the next 3K miles... What would u do?

 

i'd keep it. these cars never die and you'd just end up spending more money on a new one. check the timing belt. i just had the timing belt changed for the golf and the original looked brand new. maybe the belt change can be done later?

also, the blue book on my golf is terribly low but the car runs as fine as it did at day one so to me it's worth way more than the blue book value. these cars may be old in age but they still run perfectly.

 

Here's my two cents. If the car has a good body and I otherwise in good condition then it's worth fixing the mechanical faults. I agree with esandes, you get another car and all you get is payments and something else to fix. Do all the repairs your self for less than half of that. I just paid $500 fur my 97 A6 because the body is in great condition. It has 180k on the body and tranny, 65k on the motor and needs new head gaskets. I'm now going to just go through the car and change All fluids, all top end gaskets and seals, belts ,tensioners, plugs, brakes, filters and anything else that looks like it may need changing. Even if I throw another $1500 at it, it will still be a cheap car.
Think about it. If your car is paid for and you are spending $1500 year on repairs then that is still way cheaper than a new car.

 

If you can learn to do the repairs yourself, then definitely keep the car. You probably wont even get Kelly Blue Books fair value out of the car due to the high mileage if you sell it. The other posters have brought up good points. So...its all about how much you like or love your car.