In my opinion, Step #1 is to find a good local bike shop. Their after-sale service will help you learn the ropes; I didn't have any idea what I was looking for when I bought a new bike a couple months into starting to commute this summer, but tried a few bike shops and found one that was awesome. Building a relationship with them, learning more about my bike/maintenance and bikes in general, and still have 2 years of free service from them for the stuff that I can't do myself yet.

No idea what you're looking for, but I'd look at some of the Cyclocross bikes; I tried the Trek CrossRip Elite (which I believe is in your price range with an MSRP of $1,269) and loved it on my test rides, but ultimately wanted something with higher end drivetrain components than the Sora group. I ended up buying a Specialized Secteur Expert as it has a Shimano 105 drivetrain, still loved the ride, etc.

Commuting in the rain in Seattle though you'll probably want to at least consider disc brakes. May limit your options, but everyone tells me they perform better in the rain. I haven't done any head to head comparisons myself, but found once they were broken in, the discs seem to handle a lot nicer than my old rim brakes did.