There are buses to the airport that run all night and cover pretty much all of Hong Kong, but a taxi should only run him US$50-60 from Hong Kong Island. The Airport Express does shut down at night, however, and IMO that's the best way to get back and forth from the airport.
Asian girlie bars are a different breed, although it appears their extortionist tactics have been exported! The HK girlie bar scene sprouted up specifically to cater to the US Navy's needs during shore leave in HK during the Vietnam War. The navy still stop off in HK when China isn't playing political games and preventing their ships from docking in HK. I would say thats when the Wanchai bars (and the girls who work there) make the most money!
I would give almost all bars in Wanchai a wide berth after we were drugged by a bartender in December '12.
As far as travel, I spent my entire youth jetting somewhere or other, and had spent a lot of my summers in Manhattan, Queens and NJ, so it wasn't too much of an issue moving to NY (especially with family there). I do miss it, but I think Europe might just be the place for me now.