I have been playing to audiences for over 50 years, but still learn from the "pros" that have had more experience, and experiences. Your question is very interesting to me, as I, like others, never know for sure what goes over the best. I suppose the trick is knowing your audience and being able to tell polite applause from sincere appreciation. I thought you could merely judge the age and play songs from their era, but, as you say, it doesn't always work out.

Good topic and post.
Bernie