I've looked at both Mono and Grasshopper a couple of times and here are my brief observations.

Both claim to have good support for MS code but 3rd party objects get sketchy. Grasshoppers says it might be able to work on compiled objects, but recommends you switch to native Java libraries.

It seems that Mono will not currently run on IBM i.

Grasshopper outputs Java, so the runtime should not be a problem. Unfortunately for me, it requires a paid version of Visual Studio 2008 (which is the one version I don't have).

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