Six figures a year is possible bartending here. I recently got "regulated out" of the mortgage industry, so I'm working at a medium sized restaurant on the U St Corridor (which isn't as lucrative as Georgetown, Dupont or K street) and I'm bringing home 500 - 700 a night on Fri/Sat and 300 - 400 on other nights. My restaurant capacity is only 99 customers and the focus is on providing a good vibe, quality experience with live Jazz/R&B every night Vs. a "club" who's focus is on volume and high prices and being "seen there". In other words, I'm ALMOST at "six figures" and I'm not in the "best neighborhood" or a high volume spot.
I'd say I'm an above average bartender with my "people skillz" LOL but it's more "old school" at my place. Some of these new high end places are doing "fusion" cocktails, garnishing their drinks with pomegranate seeds and all kinds of cool shit that is in vogue these days. Half of them wont hire you unless you know "flair" bartending and can juggle your tin and a bottle fairly well. I have rows of glasses six inches above my head so we don't do flair in my bar! LOL
So the short answer is YES. You can make six figures bartending in DC if you are in the top 15% or so. You certainly wont do that starting out and it really is WHO you know! But at the same time, you have to come correct with the drinks. Breaking into it can be difficult (there's no way I'd have been hired here if I wasn't good friends with the owner), but it's not a bad gig in a pinch. It's certainly "recession-proof"!
The cool thing about it is that I would hardly call it "work"! It's like that Dire Straits song - "money for nothin' and you chicks for free"! LOL It's also cool to hang out with other restaurant owners and the "after hours" crowd is always entertaining. It's a cool scene. SOOOO much less stress than mortgage - I feel like I'm on vacation.