We have a 65 pound Boxer/Lab, and an 85 pound Anatolian/Great Pyrenees. We've done plenty of 1,000+ mile road trips with the Boxer, but the Pyrenees doesn't enjoy the car all that much, so that's limited us on distance.
As for flight travel, we're in the same boat as you. We've debated plenty of times about trying to take them on a short stint somewhere. A long haul really scares us.
When we do travel without them, it sucks. We miss them like crazy, but lucky for them they have two sets of grandparents that take them. We also buy several days at doggy daycare so the grandparents can get some days off in between.
We love our fur babies to pieces, but it definitely makes traveling, especially for longer periods, all the more difficult.