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1999.5-2002 have the VE pump ALH engines, 2003-2004 have the Pump Deuse engine and are more sensible to proper spec oil than ALH engines. Ideally you would pick a 2001-2002. Stay away of automatics, few autos of these years make it past 150k miles before needing to be replaced.
As far as the engine goes. My local TDI guru has a 2000 with 500k miles on the odo. TDI engines can take a lot of abuse, but no neglect. You have to stay on top of maintenance. Timing belt changes are not all that expensive, you can find a local TDI guru on TDIclub that will probably do it for 500-600 bucks. Not too bad since you only need it done every 100k miles. Apart from that maintenance costs are roughly the same as running a gasser on synthetics. The local gurus know their stuff and are way cheaper than the stealers. There is a great community built around TDIs, lots of knowledgeable folks that are always willing to help out.
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