When the trip is equal to a week or longer and is between 600 and 800 miles, I usually drive. If a week or less, then I'll fly. If I have to go from one meeting in Orlando to another in Myrtle Beach, then I'll fly to Orlando from Pittsburgh, from Orlando to Myrtle Beach and from Myrtle Beach back to Pittsburgh.
When it's family vacations, we will take our bicycles with us. We definitely drive when we go to Florida in January of each year and stay for 3-5 weeks, ending up in Hilton Head and then driving back from there.
When flying, I prefer to fly Southwest because there is no extra charge for a checked bag and they have always treated me well. If Southwest doesn't have the route, then I'll go either American or Delta. Both of them have been good carriers for me. I am looking forward to trying out Breeze Airlines, a new player in the market. I heard a couple of rave reviews of all that is provided at a decent cost with this new airline. When I get the chance, I'll try them out!
For booking Southwest, I'll usually book the lowest fare possible. For American Airlines, I'll often book Main Cabin instead of Economy because I can get better seating, earlier boarding, and have a free checked bag. If flying Economy and paying extra for a checked bag, etc., it's not that much more to go Main Cabin. AND... sometimes, depending on which flight you book, you can get a first class seat for not much more than the Main Cabin. (Of course, at other times, it's WAY more.)