Couple of thoughts for some options just in case the ironwork doesn't fly::laughing:
Get a farmer near you with a JD kick baler. Stand in the pan with the new rope end in your hand and have him toss you up to the top of the pole. As you fly by, neatly tuck the rope end through the top pulley.
Buy a hot air ballon ride and get picked up at home. You should be able to guess the rest.
Find someone with a 40' hay elevator. Crank it up and walk the plank. Extra points if a buddy can run the motor until you just get to the top.
Stack firewood and crawl up there in your best scaffolding style.
Use a bow and arrow to launch a designated round up to the top and through the top eye. Make sure the string is long enough to make both ends meet at the bottom level. Might take some practice but at least you won't have to leave the ground.
Hire a neighbor kid to climb up to the top.
Buy a drone and use it to hover over the top ball. Add a jib arm to thread the needle, so to speak.
Slip a $50 to a local electric company repairman with a boom truck. Tree trimmers do 'guvie' jobs, too.
Buy a new pole and install it properly this time. Cut down the old one and sell it on Craigslist for much more than the new one cost. Include a free flag (made in China of course). I'd wait for a few choice holidays for this option (memorial Dat, July 4, June 6, etc.
Plant a fast growing tree and be patient. When you get the job done, you can cut it down and heat your house.
Change your cable or internet options to satellite. Tell the installer you want the dish 'up there' ...
Check with your subdivision's Home Owner Agreement terms. Maybe a patriotic flag is forbidden because it may insult some of your illegal neighbors. Might want to do this one first, It sure would save a lot of time and trouble.