I will drive 600-1000 miles but I'm a whimp and will break it into 300 mile stops and make a road trip out of it if at all possible.
When we were doing the long distance relationship thing (L.A. to Portland OR. = ~1000 miles) we spent every other weekend together... people would ask if we drove back and forth! It is a 90 minute to two hour flight, to us it was a no brainier... had FF miles on Alaska and JetBlue... I was on a first name basis with the bartender at PDX.