I'm in Mi. and have a lot of wind at my place. I encased 12"x4' of concrete using one of those cardboard type cylinders from a box store. I set anchor bolts as my alum. pole had a base plate. That 4' has worked out just fine.
I assume you plan to bury the pole 5'? What type of soil do you have? What type of fabric on the flag? 30' offers quite a bit of leverage. Is your pole tapered? If so what's the diameter (at ground level). Is it possible to pour concrete around your pole? It'll certainly help in preventing your pole from working the soil around the pole and pitching it in the direction of the prevailing wind.