Ty - Updates and Logs

Hello,
Long-time listener (and I've asked a question or two before both here
and on the lists that Allan has helped me with).

first, I wanted to plug IXSystems. I ordered a server for my house and
it was built and shipped really quickly. The sales guy I spoke to was
really helpful in getting it when I wanted and customising it just the
way I wanted. Also since I am totally blind and can't read the manual,
when I had a question as to why my server's fans sounded like a vacuum
and wanted to power them down some since they're sitting next to me,
the engineers read the manuals, described the beeps I might get and
also gave me step-by-step instructions on how to fix the fans in the
BIOS so that I could get someone with working eyeballs who might not
know anything about BIOS config to help me.
(Off air), Although I did get my system, the accounts weren't set up
and I couldn't log in. The sales rep I spoke to confused me a bit
because he told me he had a few years of unix administration
experience, but then was confused and wanted me to type in the # that
you see on the root prompt, not realizing that it was the prompt and
not the command. Regardless of this though, he spent extra time
helping me and talking to the engineers to find out how to get into my
system.

I did have a few questions and I wanted to ask here because Allan is
always talking about ordering new servers. I presume he has a ton of
them and while I'm not getting to that point, my number of servers is
growing.
1) What do you prefer for deploying multiple systems? I really want
eventually to skip the whole freebsd-update when a new version comes
out (10 to 11), deploy a new system on 11 and just swap over the IP on
digital ocean. I also want to be able to spin up and down servers as I
like. How do you handle per-system configuration with the deployments
where the deploy on a web server vs a database server might have
slightly different configuration?
2) How do you manage updates? e.g: If I have 10 servers and each
having 5 jails, that's 50 pkg audit -F I need to run.
3) How do you manage logs? Do you have a prefered method for
monitoring and keeping track of issues so you don't need to read the
daily weekly and monthly updates for x systems? Any other advice/tips
would be greatly appreciated.
Thanks,
- --
Take care,
Ty