IronPython is directly developed and supported by Microsoft (under the awesome technical lead of Jim Hugunin!), AND has an insanely great book about it ("IronPython in Action", which I'm biased about but nevertheless evangelize shamelessly). Apart from that, Boo appears to be a great contender, and I'd love to try it out (were I ever to use .NET in earnest rather than as a for-fun endeavor -- as my professional development these days targets Linux and Mac, not Windows, that doesn't seem a likely prospect).
If you're using .NET as your main development target, my recommendation is to pick a few small but not toy projects in your area of expertise and develop each of them in both Boo and IronPython (alternating which one goes first) -- after you're through a few, you'll KNOW what's right for you. That's how I ended up switching from Perl 4 to Python as my main language back in the '90s (rather than sticking with Perl 4, of which I was an expert and guru, or switching to then-brand-new Perl 5) -- a few "pilot projects" fully developed in each environment left me with no doubt about what was best for my own productivity.