Reddit reviews How To Make It in the New Music Business: Practical Tips on Building a Loyal Following and Making a Living as a Musician

This book has gotten a lot of kudos. The author also offers seminars and has a great blog.

As for booking, you have to walk the line on being polite and being persistent. It will be a lot of rejection, and a lot of people (bar/venue managers and bookers) who keep odd hours and are frankly bad at communication. At minimum you need a good-looking website with music, photos, bios, etc. A facebook page is good as well. Over time, you will develop a relationship with the bookers. You will find out what places work best for you. Keep a spreadsheet or document on venues, who books them, their best contact method, what hours they work (many of them only check the booking email address when they're physically in the bar office, and it's like the last thing on their list). If you don't hear up, follow up every week to two weeks. Keep it polite. Short and sweet is the best. Every email should include a link to where they can check out the band and listen quickly. Do not ever send attachments. Check the email frequently. A lot of times getting a gig means writing back to the booker while they are still sitting at the computer. For festivals, it's a bit different, you typically need more professional press kit and to submit yourself to a local / regional fest booking organization, and/or privately run festivals. It's a fucking pain in the ass. If you get in with a regular / semiregular situation, treat it like gold. Do not overbook yourself, tip the staff, try to bring people out, be super on time and polite. That's all I got at the moment.

Before you do anything, I highly recommend reading two books.
https://www.amazon.com/Need-Know-About-Music-Business/dp/1501104896
This is the industry standard for a music biz 101 crash course. That's the edition I have, I'm not sure if there's a more recent one.

And also
https://www.amazon.com/How-Make-New-Music-Business/dp/1631491504
Ari focuses on building from the ground up, while the Passman book is more of a reference or "state of the industry" kind of thing.

Read these books and you'll have answers to most of your questions.

I haven't read the entire thing yet, but Ari from aristake.com released a book recently. I've followed his blog for a long time and I think it's a good read. Here.

Read
https://www.amazon.com/How-Make-New-Music-Business/dp/1631491504/ref=sr_1_1?ie=UTF8&qid=1488291061&sr=8-1&keywords=how+to+make+it+in+the+new+music