It's a ridiculous comparison and it's meant to me. The two are designed for two completely different types of people and two completely different types of driving.
Mashable doesn't seem to see the distinction. Last week they did a 'WordPress vs TypePad' poll, and it's just as ridiculous as the 'Convertible vs Pickup' comparison - the two are designed for two completely different types of people.
WordPress' template system is simpler and easier to understand. If you need to heavily customize your blog then you are probably better off with WordPress (Having said that, I customize every client's TypePad blog and so so with only a few CSS changes. I never modify the templates themselves).
The big issue is this: Do you have the technical ability to host your blog, and understand all the maintenance issues that go along with it? New Wordpress versions seem to appear every month. Yes, WordPress has made the upgrade process easy, but is your theme compatible with the new version? Are your plugins compatible? What if they are not? Are you prepared to handle it if something goes wrong?
My clients are business owners. Their business is running their business, not running their blog. For most of them, TypePad is a better choice.
