Purpose, Objectives, and Scope. Take a minute and define why you are doing the migration (purpose), what you expect to accomplish (objectives), and the limitations of the project (scope). It's a good idea to establish these parameters to keep the project focused.
Prevent this from happening by installing an unfurl sleeve at the top and bottom of your flag. With these sleeves on the flagpole, you can attach your flag to the sleeves. As the wind blows, the sleeves will rotate around the pole, preventing the flag from wrapping around the flagpole. Unfurlers of this type are for use with bracket-mount household flagpoles that are an inch or less in diameter.
Compared to the method you're using now, a vertical flag pole is tangle-free, though putting down a footing for the pole and caring for the pole and its hardware can be a lot of work. There are other solutions, some of them quite simple, such as displaying the flag vertically.