I hated Vic the first time I watched DS9, utterly cringe worthy.
Like most things I ended up just fine and kind of fond of him after a few more rewatches.
I agree with 3rd Nacelle though, show us a huge nostalgia for something NOT US. Another planet or a time in our future. So much potential there.
I guess the funny thing to me is I couldn't give a rats about Sinatra and Vegas and that era and I can't fathom why it would be interesting to people on DS9. Surely there were glory days as Earth rebuilt itself post first contact, and glory days when humans colonized Mars and settled on other worlds that people could be nostalgic over. A MARS NIGHTCLUB! It's not that hard to be really really sci fi and cool with a fictional nostalgic time.