My wife and I are in our 60's and 70's and we covered our 25 foot Dutchmen for the winter.
As some have suggested, we tried to lift it into place with long poles from the ground. That was too unwieldy for us. So we plopped it on the roof and unfolded it with each of us on a ladder on opposite sides. We did use the poles to hike it over the AC.
A bit of a pain to get centered and draped properly but no more so than scooting on my back under the TT to fasten and snug up the tie strap.
Like waxing the TT, it is something you just do because it needs to be done.
I like a cover because we park under a lot of pine trees in the winter. Others are perfectly content to leave their TTs in the open.