Interesting thoughts here.
With (literally) two weeks of university left to me, and the imminent burst of available time after, I might go back and poke at my vague idea to set up a venue. I think there might be something to the idea of keeping it active by means of regular events. Not like there's a shortage of precedents around.
Of course, as someone recently remarked to me, there's no shortage of bar-type locales. There's a good reason for this ('you walk into a tavern' is a fine staple of DnD), but it's not particularly good as a way of distinguishing yourself.
Perhaps the answer, combining several thoughts here, is a Caprica-esque V-world. Visiting places by holo is pretty accepted practice, though I personally have always gone with the interbus option... I'm a little bit of a recluse sometimes, so I'm not sure how many pure VR environments are out there, but it does feel like it provides more options. Regular (weekly?) change in 'location' and theme, perhaps kicking off with some minor event to introduce the new phase, with regular (monthly?) larger ones just to keep awareness up... VR stuff also nicely solves the question of you piratical types having cope with law enforcement, no? I personally have never let it stop me going anywhere, but if you think about it...
Personally I have fond memories of being able to surf through the Gate, the Skyhook, the Keep and the Broken Piano depending on my mood, and being able to just slip into an exchange with someone. By all accounts, such practices are dying out somewhat.
Don't mind me, just thinking aloud.