Try and get a later one. The earlier ones were a bit iffy. 2007-onwards weren't too bad.
Bare in mind the higher costs of servicing, especially with brakes. Don't worry about a 4Motion (4WD) one, unless you absolutely feel you need one. They also chew tyres.
As for things that go wrong, sometimes they crack exhaust manifolds, EGR valves are known to play up.
Like any European car, find one that has a good maintainance record. Servicing on time, everytime, by a VW dealer, or reputable specialist will land you a decent bus.
'07 Transporter 1.9 TDI
'01 Beetle 2.0
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