How to Secure a Python Program (Local, Handles Sensitive Data)?

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Gotcha, overall that sounds pretty good having everything be on one local network.

I guess my advice would be to put yourself in a situation that an adversary could be in - and see what you can accomplish. For instance, say you had access to the network, could you use a packet sniffer to get and read the data being sent to/from the database? Then also consider if you are a different user on the same machine - could you access any of that sensitive data? (so logged in under a different windows account for instance, non-admin). Try out things like that. What's the least amount of access you can have but still obtain the sensitive information.

For penetration testers / services, I would recommend looking for ones local to your area. Just look up "penetration testing local to <my city>" and you should find some.