My first jazz guitar book was Mickey Baker Book 1. I was working at a music store and I think I only paid a couple of dollars for it. Turns out, this book is priceless.
I still use the chords from this book all the time, and the way the exercises are laid out and they build on each other taught me a lot about how to get good at something new on guitar.
I also bought book 2 right around the same time, but it sat for quite a while because the chord voicings were too hard for me back then.
Mickey Baker Jazz Guitar Book 1: https://amzn.to/2URFZwI