It's like buying a car: each one of us have a bike/brand we seem to lean towards more. Do you have quite a few bike shops in your area where you can go try some bikes? My personal preference is Trek, some of the ladies prefer Specialized, quite a few of us ride customs. As I said, it's like buying a car - maybe surf some of the bike websites til something grabs your eye, see if your dealer carries it and give it a ride.

As for WSD: again, some women prefer WSD, some hate it. Both my road bikes are non-WSD (actually they're vintage bikes so I guess I"m not much help there! lol). You should really ride several different types to see what you feel the most comfortable with. Kinda like buying shoes!