@Larry_Russo - I suspect your root fault is not how you manage turning it off an on again, and I think people may have missed what was going on here. It sounds like the same issue I had with my Pi that it become unresponsive over the WiFi if left for long periods of time....
Can I ask - is the Pi a Pi2 with a Wifi USB dongle plugged in? If so - there is/was an issue where the config of some USB Wifi was set to "sleep" if there was no activity. When it goes to sleep - you loose your connectivity to your OctoPrint server, and thus can only "wake" it by booting it.
My Octoprint server would work perfectly if busy, but (I leave my Pi on all the time) if I left me printer alone for some days and came back to it - the Pi was on, the printer was on, but there was no activity on the USB WiFi dongle, so I had to reboot it to bring it back to life. A simple config change on the dongle script forces it to "stay awake" all time.
Let me know if you are using a USB Wifi Dongle, and if so - what make...
Given the low cost of the Broadcom wireless chipset, it appears in many USB-based add-on wifi adapters. Unfortunately, the standard set of widely-available drivers for this chipset don't adequately manage the power and sleep states of the NIC.
People like to sound scary about cutting power to linux, but it uses ext4, a journaling filesystem for the linux parts, so unless you suddenly cut power while it is writing a fat32 partition, like the boot partition, it should be fine.
..and I leave mine running 24/7
Also, it's handy to leave a little usb keyboard connected to it, like one of the rii illuminated keyboards with built in trancpad, they are tiny, and as long as you can issue a ctrl-alt-del key combination (check, becasue on some you can't...easily) and then just rescript that to be shutdown instead of reboot. Makes blind shutdowns much easier.
I wish there was a way to issue a shutdown via phone when there's no computer or keyboard in the room with the Octopi. I have to go up and down stairs to do the shutdown and powerdown sequence. Octoprint Anywhere doesnt support Shutdown.
Yanking power out from under a running Linux system is a Bad Idea, and it's easily avoidable. It should be a last resort for dealing with an unresponsive system, not something you routinely do.
