I purchased my 2000 Jetta in 2010, and for that car it depreciated a ton over the next 2 years. I spent $5,000 on it and within two years KBB had it valued at a little over $2,000. I have had various problems with it, some have been expensive, but most have been routine. Luckily I found a friend of a friend that does really great work on cars at a very affordable rate. He replaced my engine and clutch for me for about $2,000 a little over a year ago.
Maintenance on VW's is a little weird. German engineers like to make specific tools for most repairs (e.g. it takes a special tool to remove spark plug cables) and they add a lot of things that just seems to cause more problems than help. I have problems with this handy little security feature called the immobilizer that does not let your car start if the ignition doesn't detect the correct RFID located inside the car key. In addition, if I detach the battery, I have to reset the security system. Also, a lot of maintenance tasks can be fairly involved because the engine compartment is designed for efficiency rather than ease of access. As an example. When I want to replace my headlights, I have to remove the battery in order to access one of them, which also means I have to go through the security reset process.
My car is also nearing 200,000 miles, so it would make sense that it has more problems. I spend, on average, about $600- $900 a year on maintenance, and with the relatively new engine, I could see this car going another 100,000 without extensive problems. I have enjoyed this car moderately, but if I was purchasing another one today I would probably pick a Japanese car, such as Honda or Toyota, over another VW. Mostly because those cars are much more friendly to amateur mechanics.