Look at the top of the forum and explore the site, there are buyer's checklists for these cars. IMO, maintenance is key to having a long life out of these cars. Because of that, I would go with a new one and start from there. The 1999-2003 ALH engined Golf/Jetta/New Beetles will get the best fuel economy but these cars are getting old. If you can afford it, get a new car. If you are willing to spend money on maintenance and/or do your own work, or are willing to accept that older cars break down more often, go for the older one.