In the middle of the night, I woke up and laid there and designed an anemometer elevator for those who aspire to greater heights than they can achieve.
A post as tall as you want, with a garage door opener mounted on it vertically... Add as much track and chain as is needed to achieve desired elevation.
Mount the anny and transmitter on the trolly.
You'll probably have to hack the limit switches, or add new ones.
On a more serious note, it seems like it might be feasible to rig up a similar, manual arrangement on a flagpole. You'd need to fab up some sort of dock at the top to keep it secure and aimed correctly.
(FWIW, the garage door opener elevator idea isn't original to me. There used top be a shoe store in town with the repair shop upstairs. They used an opener as an elevator to move pairs of shoes up and down.)