It sounds like you're having fun! Can you talk about the process leading up to the first session? What are some things to consider? I wouldn't mind going out into the wild and setting up to play a few tunes. Of course, with fall and winter coming, I might not have picked the best time to get started.
Hi Nick, long time no see! How's the Filuzzi coming?
I think the main thing up front is to prepare your memorized repertoire. I've tried using sheet music, and will use it when I run out of memorized but it's not so good. You have to worry about wind, and you miss the important eye contact. If you do, you need to have something to hold the stand and music sheets in place. If you do need sheets, you can know the songs well enough to glance up and down.
Like Terry says, the repertoire is not as important as presentation. You have to prepare yourself to smile and appear to be having fun. This means concentrating on the people, not the music. I think your Filuzzi tunes will work out just fine, especially for certain locations in your area.
Another thing to prepare is improvisations. It helps to stretch out your songs. Not just because you need more repertoire, but because it's good to keep playing, and just playing the tunes over and over gets boring for you and the audience. I tend to like to do simple arpeggio improvs in the song rhythm over the chords. Preparing this in advance is good.
Now, your attitude. If you don't like it don't do it! Get in the mood of thinking about having fun playing for people rather than it being a job. Again, I don't need the tips I get, so they are gravy, not pay. Even if you need the money, act like you don't. Many people will simply ignore you. Some will throw in a dollar before they even hear the music. Either way, no problem, smile, smile, smile.
On the same note, plan to interact. The people are recognizing you, so return the favor! I'm a big fan of a heartfelt "Thank you so much, I really appreciate it."
Other than that, bring water and food if you need it, warm (or appropriate clothes) and light gloves if necessary. I like distinctive clothing, bright and with a hat, of course!!!! A coppola is recommended!
Anyway, you can do it!!!!! You are a good enough musician, start slow and see how it goes. Good chance you'll meet other musicians and the Bolognese gigs will magically appear. Good luck amico mio!
