Disclaimer: I only dabble in either language, but I have at least written small working programs (not just quick scripts, for which I use Perl, bash or GNU make) in both.
Ruby can be really nice for the "multiple paradigms" point 3, because it works hard to make it easy to create domain-specific languages. For example, browse online and look at a couple of bits of Ruby on Rails code, and a couple of bits of Rake code. They're both Ruby, and you can see the similarities, but they don't look like what you'd normally think of as the same language.
Python seems to me to be a bit more predictable (possibly correlated to 'clean' and 'sane' point 2), but I don't really know whether that's because of the language itself or just that it's typically used by people with different values. I have never attempted deep magic in Python. I would certainly say that both languages are well thought out.
Both score well in 1 and 4. [Edit: actually 1 is pretty arguable - there is "eval" in both, as common in interpreted languages, but they're hardly conceptually pure. You can define closures, assign methods to objects, and whatnot. Not sure whether this goes as far as you want.]
Personally I find Ruby more fun, but in part that's because it's easier to get distracted thinking of cool ways to do things. I've actually used Python more. Sometimes you don't want cool, you want to get on with it so it's done before bedtime...
Neither of them is difficult to get into, so you could just decide to do your next minor task in one, and the one after that in the other. Or pick up an introductory book on each from the library, skim-read them both and see what grabs you.