Well, after so many confirmations and few bugs worked out, I felt good to try and went for the update. All went good, only about 20 seconds downtime from the database update portion.
One thing that's so annoying, is needing to SSH into every server and manually run package updates. It's such an annoyance - even on the small cluster I have now (2 hosting servers, 1 standby hosting server, 2 dns servers, 1 main control server, 1 backup server)... That's 7 servers to login to and run the package updates, bwuhhhhh... I need to find that Feature Request to be able to run updates from the control panel and up up UPVOTE that thing lol