A maksutov or shimdt-cassegrain telescope wont make the images look upside down. They will look mirrored though...
I've read the titles on the airplanes and seen ground equipment at MEX
from 10 km away at my grandfathers apartment. It is a rather small telescope (3.5" dia.) but the quality of the image is as good as an 8" dia. Mind you, it is a $4000 dollar telescope. Also he uses a tripod that was originally used for mounting video cameras in TV
studios back in the 70's. And yes it is very very sturdy, extremely heavy and industrial sized!!!
Although this $500 'scope will do the job fine:
Google for MEADE or CELESTRON.
I'm also a bit into astronomy, so if you want to know about scopes, let me know.