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As a lot of more experienced jazz musicians will attest, there is nothing better than playing in live venues with other musicians to rapidly improve your playing and build a repertoire of memorized tunes which you need to have in most jam settings. So where do you find live venues and other musicians to play with - especially if you are working on gypsy jazz stuff?
Coffee houses are a great choice and the typical vibe works well for acoustic gypsy jazz. GJ is not too loud or distracting and seems to engage a lot customers who tend to stay longer and spend more money and leave bigger tips.
Finding the right coffee joint can be a challenge. Seek locations that have a nice sized room where you can perform without crowding out patrons. Saturday - Sunday afternoons are best IMO as this is good time for many folks to grab a Joe and relax before they head home or go out for the evening.
If you are new to playing live, practice tunes with another guitar player and add a bass if you can before you play in public so you sound decent. Check out coffee shops in well trafficked locations and ask the manager/head barista if you can play acoustic guitars. If you exude confidence, most will at least let you do a few tunes to start - and that could build into some weekly jams with buddies that, like you, would love to play in public.
Don't expect or ask to get paid. Free drinks are the best you can hope for - and you may need to put a few bucks conspicuously into the barista's tip jar when you finish to insure a warm welcome on your return. Once you get a steady thing going, you can place adds in craigslist for other musicians if needed and have a nice outlet and practice venue that could lead to paying gigs from gratified patrons.
I have more to say, but I'll reserve my additional comments to await feedback from others.