Dealing with proxies and remote setups can definitely be a maze sometimes. When I had to connect python scriptes to databases through multiproxies, it was really difficult
One thing that might help is ensuring your Python environment is set up to handle proxy chains correctly. Sometimes libraries like requests or pymongo can be configured to pass through multiple proxies. As for rotating proxies, services like Proxy Rotator can be a lifesaver for tasks needing frequent IP changes, like data scraping or managing multiple connections securely.
Just be mindful of your corporate policies on proxy usage. I once struggled with a similar setup where I needed to script connections through layers of proxies for a project. It took a bit of trial and error with library configurations, but once everything clicked, it was smooth sailing.