My thoughts:

Buy NEW if:
1. You take care of your cars well.
2. You put a lot of miles on it.
3. You intend to be in that car for at LEAST 10 years.

Buy USED if:
1. You feel any financial crunch in your life.
2. You don't put a lot of miles on it.
3. You could foresee a life-changing event (different/loss of job, marriage/kids) in the next 5 years.

LEASE if:
1. You've got the money.
2. You don't have the time.
3. You think you'll want a different car in 3 years time.


I'm 35 years old and I've never had a new car.
I'm not a fan of quickly depreciating assets either. Use Facebook, tell your world you are looking to find a car to drive, can be used. Often friends are willing to unload their current car at a more-than-fair price because they NEED a new car (job situation or life situation). When I bought my home, I bought it from a friend's aunt. I got a full disclosure on the ups/downs to the home and we saved 3% with me not getting a real-estate agent.

When we had our daughter 3 years ago, we bought our first new car (for my wife). My wife has USAA afiliation (through her dad) and they have discounted rates - which are pretty-much no-haggle. We used consumerreports.org to select our vehicle.

Regardless of buying New or Used, I'd suggest going to this site and reading EVERYTHING.
http://www.carbuyingtips.com/
You'll be prepared if you do... and spending money on their guides for the car that interest you are well worth the money.
It's not the cleanest website in the world, but I read almost everything on there before buying our vehicle and felt very comfortable about the auto-buying industry after I had read so much.

Good luck.