If you do your own service, you'll love these cars. The one catch is getting under them, because the belly pans need to come off for most regular services (e.g., oil changes). That's why I installed a lift in my garage. As others have noted, there's a lot of expertise in this group if you want to DIY.
Re price: just get out there and start looking and making offers. Nobody knows what a car is worth until a seller and buyer agree. The car looks great in any color, so don't confine your search to only one color. I started out preferring the white with blue stripes ('cause that' was the Hot Wheels toy I had as a kid) or blue with white stripe, but I ended up really liking the red with white stripe--besides, everyone knows red is the fastest color! The more you inspect, the more you will become familiar with their details and what to look for.
If you want a really pristine, 4-digit odometer car, I'd say go see Shelby at Elite and pay the price. For a driver, there are plenty of choices. And just to beat the dead horse again, be sure to get a PPI by someone knowledgable.