Hi,
I am managing 25 Hetzner baremetal servers, and have experience in raid replacement, sysncing and managing.
Youe have requirements that spread a lot. I can help you out in replacing faulty hard drives, and backups, also can setup an automated backups for you so you don't have concerns about that.
updating Drupal form 7 to 8 is not something I would like to do. Especially if there was "custom" development for your needs.
Other tasks are fine and I can helpout with those. Ofcorse I will do the drupal update, but it may not work, If that is the case I will restore the old version and you should look for a Drupal developer.
Regards