I do about 440 shows per year, almost exclusively at nursing homes and retirement communities. I used to do over 500 before the economy went bad.
My shows are typically 55 minutes long. It wouldn't be tactful for me to say how much I get. I'm told that it's more than most of the other entertainers, but I'm not the most successful entertainer in the Chicago area elderly circuit.
I agree, $100 does not cut it here in the Chicago area when you factor in all the driving, setup, take down, time making appointments.
I think that the most important thing is to do a great job. I've been doing this for years. I know hundreds of old songs. I've learned and created hundreds of one-liners and puns. If you say something like, "My dad was a great dancer. Mostly because he grew up in a house that only had one bathroom," you're going to see a lot of laughter, and you're not going to annoy people who just want to hear music. Or, "I learned this song in second grade. I had a cross-eyed teacher. She couldn't control her pupils."
I don't know. I get consistent great feedback from my audience because I'm taking time to learn some good chops on the keyboard, I play the songs they love to hear but I don't play too many ancient songs, and I make people laugh.
I've found it helps after the show to thank everyone in the audience if I have time. I show that I am grateful that they came - even if they didn't have a choice and can't move! I feel blessed that I can get paid to play the keyboard and share some smiles, and I want to show my audience that I care about them individually. It takes 5-7 minutes.
Other factors that help are dressing nice. I'm not the best dressed, but I always come with a tie. I have a collection of music-themed ties that I always get compliments on.
A website with videos and endorsements probably contributes 10% to my business. If I create a new video (and I'm due) or get a great endorsement from the head of marketing - I make sure to email it to all of the folks who aren't using me or haven't used me in a while. So it's important to have the emails of as many of your clients and potential clients as possible. I personally don't have time to be doing mass mailings even though some might get a lot of bang for the buck out of them.
Have great equipment. I play the PSR-S910. It's not the best, but it's a great keyboard. I have a great mic and great speakers. One sign that I have great speakers is that almost no one tells me that I'm too loud.
Don't race to the bottom on price. Be better than your competition and justifiably charge more.