I've been in more than a few bands, and am currently in two regularly. One's acoustic, the other is a full rock band. Between the two, there are probably around 600 songs we've played, and can rattle off more than half of those easily. Some we haven't played in a while and we'd need to brush up on, or just listen to real quick to remember the arrangement, etc.
I end up learning anywhere from 3-10 new songs every week for my acoustic band. We're always performing and always doing a weekly song challenge for us to come up with acoustic arrangements of songs that aren't typically acoustic, like Tool, Toto, SRV, Motown, etc.
My advice, just play, and play, and play. If you like playing, it's not work and you'll always love what you're doing.
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2011 Martin D28 Sunburst | 2004 Taylor 310CE L7 | Mesa Boogie Rectoverb | Fender Super | Custom 1998 American Stratocaster | Yamaha Alto Sax | Ibanez Basses | Ramirez Flamenco | too much else to mention
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