Drop Bar Commuter in San Francisco

Your level of experience with cycling

Entry-ish. I've taken the beginner internal and external bike maintenance courses at my local co-op and have a basic familiarity with bikes, but don't really know that much about the market.

What's your price range, and have you considered second hand?

<~$1200 kind of flexible. I have considered a second hand bike, and have no issues whatsoever with it. I just don't know if it's right for me given the second hand market here.

What's your intention with the bike - commuting, fitness, touring, sport, etc?

Just commuting, mostly. Some fitness/fun rides.

How far will you be riding, and how often?

I've been bike commuting on a 2012 Trek 7.2 FX WSD (non step-through) daily for 8 months, ~50-60 miles a week in San Francisco. My work commute is 5-6 miles each way, 4-5 days a week, plus miscellaneous rides.

Riding conditions: roads, pavement, trails, single-track, off-road? Flat or hilly? Traffic and weather.

Almost entirely on (kind of crappy) city streets. Mostly low/slow traffic and congestion, not on highways or thoroughfares. Very rarely on hard-packed dirt/gravel. San Francisco, but I don't do a whole lot of climbing, 150ft or so to get home from work or go to my BF's house. It's not that bad, but I'd probably rule out any bike that's harder to get up a hill than the one I already have.

Additional Considerations

The bike that I have is great for what it is, but I realized pretty much immediately that the flat bars are not my friends. I got palsy in both hands that I was able to mitigate significantly with ergo grips & small bar ends, but I still get occasional numbness. Plus I don't really have brake access from the bar ends and I find that position to be too wide. So I'm looking for a drop bar commuter, instead. Preferably one that I can mount fenders and maybe a rack.

The other thing to consider is that I'm short (just shy of 5'2"). The sizing on the 7.2 FX that I have is 13". It isn't a step-through but it does have a weird super-compact geometry where the top tube slopes down a lot. This is great for stand over clearance and all but it's a total pain in the ass to carry around or to try to mount anything to. I live on the top floor of a 6 story building. Thankfully there's a very rickety little elevator, but I still have to carry the bike up/down at least one floor because the lobby is on the second floor. Sometimes further if the elevator is stuck. So weight is somewhat relevant to me in that regard, or at the very least a bike with a more traditional frame geometry that lends itself to being carried/shouldered.

I've also had this bike for several years and since I started using it to commute, I'm ready for an overall upgrade to a better quality bike. I feel like my budget is appropriate, unless someone tells me otherwise.

I see a lot of recommendations for cyclocross bikes (or at least cross style commuters). Is this right for me? If so, any specific bikes I should go check out at the LBS? If not, any other suggestions? Also, if you're from SF--shop recommendations!

Thanks!