Hatch A Plan: 2006 Audi A3

A high mileage complex luxury cars with scary electronic integrated gizmos should put the fear of the electron into any sane person...and I count myself in that small group.  A mid 2000s Audi A8, for instance, is going to be overly complicated and certainly cheap because it is going to cost arms/legs/kidneys/children to repair...but if you step downmarket into something like a low spec Audi A3 that doesn't have all the complicated rube goldberg auto-driving features...you might just be able to drive it for a few years and sell without doing anything other than adding gas.  Maybe.  Got a lucky rabbits foot keychain? Find this 2006 Audi A3 offered for $5,500 in SF Bay Area, CA via craigslist.

5k: Upmarket Golf: 2007 Audi A3 2.0T 6-spd

The Audi A3 was first available in North America in the second generation (type 8P) and was sold from 2006-2012.  MSRP for a brand new A3 in 2007 started at $25k and increased easily into the $30k range with a few options.  Mercifully, the magic of depreciation has lowered the prices to something much more reasonable.  Find this 2007 Audi A3 2.0T 6-spd for sale in Philadelphia, PA currently bidding for $6,700 with a few hours to go.

10k: Sportback: 2007 Audi A3 2.0T 6-spd

The Audi A3 first appeared in North America for the 2006 model year in a neat and tidy package - resembling a cross between a Jetta Wagon and an A4.  The A3 used a transverse front wheel drive layout with an optional Quattro all-wheel-drive setup added to the lineup in 2009.  Honestly with the 2.0T, power is low enough that the Quattro vehicles are slower in almost any condition except snow due to the added weight.  The A3 is one of the few cars that the front-drive version may actually be more fun to drive than the all-wheel-drive spec because while both are understeering pigs at the limit, only the front driver can do a massive burnout from a dead stop.  Find this 2007 Audi A3 2.0T 6-spd for sale in Denver, CO for $12250 via craigslist.