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Using Python via IronPython and trying to get C# to talk to Python sounds like it could have lots of issues. I would go with a Python HTTP(S) API that gets called by the Winforms or WPF UI.

This has the added benefit of forcing you into a more decoupled architecture and allows you to easily add a different type of UI (web, phone app, etc..)

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I think I prefer the RESTful API idea more than anything because it could keep the architecture decoupled. The only thing that worries me is having issues installing this to client desktops. A lot of our clients are banks and insurance companies so I wouldn't want to create issues with our installation and get things blocked by client IT.

yep, you'll definitely have to work through issues around getting network access, meeting requirements for keeping data adequately secured in transit and at rest. some places might really not want to run external servers, and run the server(s) on their premises

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