I don't have a playlist, other than what's in my Songbook on the keyboard, and that's about 50 or 60 song/setups.
I have thousand of chord/lyric text files in both keyboard and laptop and in my again head.
I just look at the audience and try to decide what they might like. After a few songs I can see what, if anything, gets the best response, and go from there.
There are a few songs I do that seem to transcend generations and audience types and I do those first, as a rule.