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It is hard.  I have used the big Rohn push up masts for a long time like since the 1980s along with Rohn25 tower.


The last time that I pushed up the 20M Moxon I had help and that was a couple of years ago but the weather turned it into a pretzel so on the ground it stays.  That was too big and heavy right from the start. 


I am 62 and this spring will be my last cycle of the push up masts.  Even with hitting the gym and being an serious athlete I find it hard to co-ordinate the mast, cable, and guys for even the simple 10M Moxon.  The good news is that they are easy to take down.


Now as far as raising and lowering I have always stood up and secured the mast while collapsed.  The two that I have up right now are roof access, I get on the roof and can raise / lower from there.   The 10M antenna is up the highest, around 35 feet with one of the sections mostly unused still in the base.


Ask the neighbor for help or the local radio club.  People like to help.


Fun times  http://trolinger.com/david/ame25/tower.html