Cycling/Commuting FROM Davis Square

[on-reserve.livejournal.com]

I know many people commute FROM Davis TO day jobs elsewhere in the vicinity so I'm hoping this question will be deemed on-topic:

If you were to commute from Davis to the Back Bay/Copley area, what route would you take? Anecdotally, do you consider this to be a beginner, intermediate or advanced commute in terms of road savvy required? What sort of comfort-is-a-priority-but-price-is-less-of-a-concern bicycle would you recommend for a commute like this?

I suppose I could have posted to b0st0n but I'll admit that I prefer the less-snarky waters of davis_square when seeking advice/opinion.