>You generally need to bring an applicable skill to the table immediately on hire.
I don't really understand this mentality unless you're talking about the first 5 employees or so.
If I find someone who is otherwise great, but has experience in PHP, and my team uses Ruby, I'd rather hire that person now and spend a few weeks getting them up to speed. The alternative is to spend even more time waiting for the perfect candidate to come along who can hit the ground running.
You touched on my next point a bit when you said a proven generalist. I think that if you have a strong grasp of CS fundamentals, and 5 or 10 years of experience, you should be able to pick up enough of almost any imperative language to be productive within a few weeks.
I don't often use Python, but I do have years of experience with C, Ruby, Java, C# and others. The first time I needed to use Python I was able to pick up enough to get by in a weekend. The first time I used haskell, now that was a bit different.
I'll leave this here. http://www.jasonbock.net/jb/News/Item/7c334037d1a9437d9fa650...