What's the Right Way to Book a First Tour?
What should you do? Pay attention (so you only make horrible mistakes once or twice), be organized (get a binder/do spreadsheets/make a little database). Be honest with everyone so there aren't unrealistic expectations. Ask for help when you need it, and be easy to get ahold of. Be concise in your communication -- persistent, creative and reliable. They are your friends but make sure you represent them in a professional manner. Don't be a dick to anyone -- but don't be a doormat either. Booking is a world where everyone is harried and effusive, seemingly, at all times. Don't take it personally.
Your work with YFB is kind of an internship. Make yourself indispensable; fill the space that needs to be filled and you will find yourself with a job. Maybe not with this band quite yet, but if you are useful -- if you are better at this than bands who don't have the time or skills or connections, people will hire you. See if you can't network your way into doing another two or three tours on a help out basis for free/a small fee (no commissions) and then start putting the word out and approaching bands that you like that have a moderate draw and are not assholes.
Lastly, why not be the CEO Of The Garrett's Hot Nuts Agency LLC, effective right now? Put it in your email signature and give yourself a title that indicates, yes, you are the boss ("Agent -- GHN Agency"). It's not an up-sell, dude. You are the founding agent of your agency, this tiny thing you are doing is building it. Get that shit off the ground and get business card official with it.
Best of luck to you and YFB,