I've played exactly 0 P&W gigs because we didn't HAVE those types of things at our church (incredibly small town). We had organ and choir. The priest actually got mad at me for bringing a guitar one time and wanting to sit in with the choir when I was in high school. I was also an altar boy from about age 7 to 16 and couldn't believe playing music on an electric guitar was somehow inappropriate.
Instead, I played solo gigs with anybody who could play any instrument or sing. At 17, my friend and I composed a 4 minute guitar duet, hand-wrote 4 copies of a sheets, and competed in a high-school band sectional competition, but the judges had never had anybody show up with a guitar before nor compose their own piece. We got a feature shoutout, which resulted in an encore performance, but they refused to score us and instead gave us a "Satisfactory" ranking. At 19 I found myself taking my metal band, putting the drummer on keys, grabbing acoustic guitars and playing a dinner party for the chamber of commerce. The guests didn't even know they were hearing Marilyn Manson songs, but that's a story for another time. Hell, I've even showed up at other bands gigs and been asked to play. I don't even know how many gigs I've put a band together by walking through the crowd and talking to musicians I knew that happened to be there.
The point of all this is years of playing all kinds of crazy crap I never thought I would do prepared me for those bar gigs where you're playing to the staff. I don't think the crowds have really changed all that much, but the music those crowds want to hear certainly has. My message to you simply is: No matter what the gig is, do it well. Perform to the bar staff as if they're a crowd of 200 and eventually 200 will show up. Perform to those people like it's a crowd of 1000 and eventually 1000 will show up. Just have fun with it.
We have a few simple rules in my current cover band:
If somebody in the band doesn't like the song, we don't play it.
All song picks have to be a top 20 hit, regardless of what year it was.
If we like the song, but doesn't fit, we change the genre of the song to fit.
If you want something done and nobody is doing it, do it yourself. Consult the rest of the band before you spend any money on it, however.
If somebody is doing something, don't complain that you would do it differently. For instance, if I'm doing merch and you want to help, you do it based on my system of merch inventory. If you have suggestions, I'll listen, but unless you want to take it over, I don't want to hear you complaining. This removes the "what if I do it wrong" line of thinking that prevents people from taking the initiative.