If you were planning on making a pep file for a flag I would recommend against it, but making the actual flag would be awesome!
You could probably just start with a regular flag pole and if you want just add an extension across to make the flag always extended. The only real challenge would be finding someone able (or willing) to cut and stitch you the logo you want. But if you want to make a cheaper flag you could just go for a nylon/plastic flag with a print on it so you could make more (different kinds) quickly if you wanted.