I have a simple python script to send data from a Windows 7 box to a remote computer via SFTP. The script is set to continuously send a single file every 5 minutes. This all works fine but I'm worried about the off chance that the process stops or fails and the customer doesn't notice the data files have stopped coming in. I've found several ways to monitor python processes in a ubuntu/unix environment but nothing for Windows.
If there are no other mitigating factors in your design or requirements, my suggestion would be to simplify the script so that it doesn't do the polling; it simply sends the file when invoked, and use Windows Scheduler to invoke the script on whatever schedule you need. By relying on a core Windows service, you can factor that complexity out of your script.
How can I monitor a python scrypt and restart it in the event of a crash? (Windows)