Edd Dumbill tried IronPython and now prefers Boo. Another Python friend was thinking of trying Boo too. The problem I have with that is I'd rather the bulk of my code not be tied to a specific platform, which Boo seems to do. Boo runs on MSFT dotnet as well as Mono, but still requires the CLR platform.
Edd raises significant concerns about IronPython. Rather than a somewhat handcuffed Boo, I would think a Python programmer would be very well off with regular CPython and bridging to dotnet via the Python.Net dll's.