I re-imaged Octopi and Octoprint and set up everything from scratch and still have the same issue.. Is there a way to perhaps go back to an older Octoprint version and see if that fixes the issue ?
Not every fault is the fault of OctoPrint.
Can you share a serial.log?
But please with more than just one incident.
What @Charlie_Powell means is, that if the USB cable is maybe touches a motor or gets bad contact due to the movement of the z-axes.
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Forgot to say: you may have to enable serial logging before data is stored in that log.
How do I do that ?
Is written here: logs
Settings > Serial Connection > scroll to 'enable serial logging'
nvm found it... It's enabled now.. Now you want me to try and make it break a few times and then share the serial.log file ?
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That would be useful, yes.
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Especially not things like a printer suddenly rebooting, ignoring endstops, not heating up, and so on and so on. That reeks of a firmware crash or mangled communication.
No downgrading, upgrading or whatever-grading of OctoPrint will be able to fix issues with your firmware or your communication reliability.
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My printer is printing fine as we speak from the SD card directly! The only time it keep rebooting is when I home it from the Octopi.local
When things work fine when printing from SD card, this does not include working fine via USB. The controller has to do quite a few things more. And if there are faults in that firmware code, things mess up.
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I understand.
Hey guys thanks for all the help so far trying to figure this out!
I have attached the Log as requested.. I Home once and it rebooted... then restart everything and it finally worked woot.. After days it finally worked.. So I restart again and Home and it rebooted again 
serial.log (8.8 KB)
New Error!
This is your firmware saying that something is wrong with the connection to your hotend. It told it to heat up, but the temperature probe didn't detect it actually heating up. Either faulty wiring in heater or thermistor, or a firmware bug:
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Jeez I can't catch a break right now
now it's printing 
Anyone can link me instructions to updating firmware for Ender-5?
Oh, it's an Ender 5! No wonder you are drowning in issues, the Creality printers usually ship with broken AF firmware.
Ender 5, Ender 5 Pro or Ender 5 Plus?
Maybe this helps:
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The reason I am flustered is that I've had the printer for a year and no firmware related issues.. and now suddenly it's all falling apart