Reddit mentions of Swing and Big Band Guitar: Four-To-The Bar Comping in the Style of Freddie Green

Let me tell you about my experience, when I was working towards becoming a bigband guitarist.

Bigband guitar is primarily a rhythm guitar. Soloing is secondary. That means you really need to know your chords. For swing, Freddy Green is king, especially if the band you are interested in has a pianist. If you'll also play funk and latino, learn block, drop 2 and 3 voicings. These will also help if you'll ever have to comp swing.

You need to know how to read and modify charts. Guitar charts are funny, many arrangers are not guitarists and don't really know the challenges the guitarist has. Therefore, the chords usually outline the harmony of the whole band, not necessarily what you play. Sometimes the charts are bogged down with so many chords with extensions that you'll never play, so you need to know how to reduce them. Another time you might get a chart that is too basic, like a single chord for many measures. In those cases you need to know how to expand the harmony, without ruining the sound of the whole band.

You'll work a lot with your rhythm section. With a pianist you'll work what parts of harmony each of you play, so you don't step on each others toes. You'll work with a drummer and bassist to figure out how each of you will play rhythmically to suit each piece. You can learn so much here, so pay attention.

Work on your rhythm a lot. Swing/groove is the most important skill. Having a lesson with a good drummer can do wonders. Every groove has a certain sound and body feeling to it and you'll never learn it from backing tracks, only playing with a good drummer will do it (my experience anyway).

So, this may seem a lot of work, but it's quite doable if you persist. Playing in a jazz ensemble/bigband can be very rewarding. One more thing. Sometimes you'll have some asshole tell you you are not good enough or some stuff like that. Never let it bring you down! In amateur band having a willingness to learn and work hard is much more important for band leaders and music directors, than having skill already. So when someone tells you your playing is off, ask how can you improve.

Sorry for any mistakes, english is not my first language.

Edit: this is a good book for starters: https://www.amazon.com/Swing-Big-Band-Guitar-Four/dp/0793573815