Re: Am I approaching this correctly?
+1 on all Jim's comments.
Also, seems like you're creating a lot of work making the backing tracks, when there are lots of online resources (like Free Bluegrass Backing Tracks [fbbbt.com] and MandoLessons.com) that have already done that work for you. Plus, on the pay side, there's StrumMachine.com which is only $50/yr and has even more backing tracks, plus the chord charts and a gazillion additional features (tempo, key change, etc.).
And you never really know how a new jam session will go as far as how friendly and accommodating the folks are, but 99% chance they'll be really nice and helpful, as they've all been exactly where you are. Especially if the promo for the jam mentions something like "beginner friendly" - or at least doesn't say something like "for advanced players"
"Keep your hat on, we may end up miles from here..." - Kurt Vonnegut
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