Im thinking of using cars as goal markers. At least initially.
My first goal is a Kia Optima EX or SX. This will generate laughs I am sure but it is a pretty damn nice car for the money. Beats the other offerings in its class like Accords, Camry etc... IMO. By the end of next year I want to have a used 2011 version of this car.
The next goal, as of now, will then be a Cadillac CTS or ATS sedan.
After than im not really sure. I cant see myself ever buying a car thats higher than the $30k range. But thats just speaking from the point im at in my life right now I guess. It gets to a point where a car is nice enough where its hard to justify spending any more. Not to mention the only local luxury dealers are Cadillac and BMW. The inconvenience of driving far to get the car serviced would keep me away from other makers. So ill have to think of different goal markers at that point.
First of all, why would it generate laughs? I can guarantee you that 99% of the people who LAUGH at your car probably don't own one (parent's cars don't count). If they do own a much nicer car (the 1%), they don't NEED to laugh at you because they KNOW that they're better than you because the car they drive is nicer (this is just one aspect).
Oh another thing I forgot to mention in my other post was that you DON'T need to go to STEALERSHIPS for work unless the vehicle is under warranty. If it's money that you'll have to fork over for a job, then go to an independent mechanic. I'm sure there's an independent cadillac specialist or a german auto specialist who targets Audis, BMWs, Volkswagens, etc.
You're going to be forking over a lot of money as milestones then you're going to end up paying for it because you're going to get hit with depreciation HARD especially if you go with newer cars.
Like my Range Rover. Brand new starts from 94k in Canada for a 2012. I can get an '09 for HALF. or even a 2010 for HALF in the states.