I've bought cars on ebay sight unseen (nice pictures) from 2500 miles away and the car did not disappoint, of course the car was only $600, but was 1400 to ship it. The last purchase was just over 1900 miles away. When the shippers started jerking me around my wife said let's just go get it ourselves, so I borrowed my brother's 4x4 Hemi Ram and took off after work. After two full days of driving we picked up the car (which thankfully included a trailer) and then pulled everything back. Sure it was a little more money than a shipper, but we spent some quality time together and picked up a killer car. Those are the longest distances traveled to get one, but I have bought cars from my neighbor (about 100 feet away) so we figure that it all balances out.
When I was 16 I wanted to go down to Atlanta,GA to buy a 70 Charger R/T SE, but my dad didn't want to go, so I had to pass on the car, that ended up with me getting my GTX. Here I am over 25 years later driving all over for parts, cars and memorabilia. I wouldn't have it any other way.