I like Marty's idea, but you can also check for the well known variable called $device_devicereboottime as well in the script. Should be in YYYY-MM-DD HH:MM S format. If Python, drop the preceeding '$'. The Python script then could run the CCS job.
Yes, you nee a cloud tab that is on your internal Network That's how I have it set up at my house, very basic 3 router setup, going to add VRFs and some other SDN, vendors ens160 us the interface on my Ubuntu Server