Not necessarily the generation you're looking for, but I daily drive a 2013 Jetta Sportwagen TDI that I bought new in Sept. 2012. Has 105k miles on it with only the regular scheduled maintenance. I've never had any reliability issues. Only issues I've had with the car, is the panoramic roof groans over bumps if there's been a large temperature change, and its done this since new. The other one is my fault, the tires will rub under hard cornering or if there's a fatty in the back seat (lowered on H&R coil-overs with VMR wheels).

I have 2 maintenance gripes. Oil changes are expensive b/c I have to buy the emissions system protecting oil, luckily the dealer sends me coupons for $70 oil changes (about what the oil costs by itself). Second, the fuel filter change (every 20k miles) requires the use of the VAGcom because the fuel system requires purging.

Other than that, my owner satisfaction is very high.

This annoys the heck out of me. My appliance car is an Accord that I bought (family purchase) with 15k on it at 7-8 years old, and the interior was immaculate, but the damn headliner was showing signs of starting to fall. Fall 2014, everything behind the sunroof and all inside corners are separated, and I am holding up the back edge with binder clips. And this is a car that, in its first ~7 years in Florida, was always garaged and driven very little. And the only way to fix it with an OE look is a replacement OE headliner - who knows if I can even get the OE fabric, never mind where.

I have currently two ALH jettas in the stable. Good cars, boring, slow, fun when modded. The keeper I have has koni's, lowered, 02j swap, bigger turbo w/supporting HG mods, exhaust out the hood, etc. ha anyways
I have worked on *cough* flipped a few beetles, and hate them. They are such a PITA to work on compared to the jettas and golfs. When they built them they angled in the frame rails, and makes access just that much more difficult.
If you search craigslist you can buy them on the cheap with problems. The one I am working on now needed a IP resealed, and timing belt, basic stuff. The one before snapped a timing belt, and was in pieces... They hold resell, and sell fast with fresh maintenance.....

I know the Mk3 Golf Turbo Diesel are almost bullet proof. Even though they're over 20 years old they're still worth good money now.
A fellow VW club member has over 600,000 km on his and it's still on the same untouched original motor. (second gearbox)

I can't imagine the newer ones being as good though.

Your local VW wrench will be happy you bought that car.

My wife has a 2002 5sp TDI Beetle, which we bought new in fall 2001. The car is on its 2nd timing belt at 200,000. Aside from one set of rotors/pads, everything is original. The only weird things are electrical: the locking system, which will lock on its own. It has done this since new. We never start the car, close the and walk away. Also the turn signal relay has an intermittent spastic attack in the dash. It doesn't flash lights just makes noise. I replaced it and it continues spazing out intermittently. I have replaced the 109 relay glow plugs a couple of times.
The car gets over 50 city/hwy except in winter when it drops to low 40s, We have gotten 60 mpg on a couple of trips (must have had the wind at the back).
Turbo has plenty of power, manifold is not plugged, and burns little oil between changes.
Car has been a keeper and we are looking forward to the next 100K.