Have you gotten arcpy/arcgisscripting to play well with in IronClad? I haven't ever been able to get it in any sort of working state that I'd trust in production.IronPython is great, but if you're going the .Net route you're going to need to use ArcObjects and the .Net SDKs. You get Python syntax to do your coding in but you're in a totally different development environment.
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