Assuming it has oil and not damaged i would say the brass unloader valve in the head. When you try to start it, push down the little brass "pin" on the top of the unloaded valve see if intakes off then. My was sticky, and also mine would have issues using an extension cord plug direct into the outlet.
Thank you again to everyone for their input and suggestions. I have got it working but it requires a
strange step. This has gotten quite interesting to say the least.
Update Video:
To recap:
-After reviewing the manual, whatever is going on is tripping the Automatic shutoff system. I've attached that page with the information on it at the bottom. Both possible causes that it mentions don't apply here.
-The compressor does have oil to the fill level
-I tried starting the compressor with and without the air filter, no difference.
-I'm not using an extension cable.
The way I've gotten it working is by opening one of two things. Either I unscrew the brass unloader valve at the top (it's called the start valve on the manual listed as #2) and it starts right up as you can see in the update video, or I leave that part attached and instead unscrew the unloader tube that (#60 on the manual).
[Interesting side note, one of the first things I did was try to start the compressor with the unloader tube unscrewed and it didn't start then. The video is above in this thread. It did seem like it was making progress but it couldn't start still. It now starts up with the unloader tube disconnected.]
I've attached the images of the two parts I'm referring to here:

<--- Start Valve

<--- Unloader Tube
Either way, I have to essentially screw them back on while compressed air is being pumped through whichever part is unscrewed. It seems like I have to do this
EVERY time I try to get the compressor started. Regardless of if its got pressure in the tank or not.
Again, I have no idea how compressors work, but it seems to me like the compressor can't get started when there is some kind of resistance or in this case in the form of air pressure. I could be completely wrong but I'm curious what others with experience think.
I feel like I'm so close, any help would be super appreciated.
Attached are the pages referenced from the manual:


