Hi @Zooey,
I’m late on this thread. Whew! This seems like a lot of work! 
However, people are correct here, you need to be careful with the updates. Yeah, don’t touch the main site, and use a clone or staging site.
We fully support ClassicPress hosting, and could easily make you a ClassicPress staging site, so you don’t need to touch your main site. Also, the Installatron App installer (which we have) will easily make clones.
We could even install UpdraftPlus for you, so you can make all those auto-backups before updates. More importantly - roll back if there are problems. We have this setup for our WordPress clients. I just tested that environment yesterday for CP:
Message me directly if you are interested, and we will get you setup on the weekend!
Cheers
Avrom