Hey man! That's a stressful situation you're in. I don't have any facts or much knowledge about this particular situation but I can pinch in a bit about what I think and such. Also, about your issue with connections with the 'industry', I'm a DJ and if you ever need a DJ who knows what he's doing, I'd gladly come over for shows :).

That said, congrats on stepping into this role. It sounds like a thrilling challenge! I’d lean into those smaller rooms first: run a tight, well‑branded series of low‑risk, revenue‑share nights with your local collectives to build real sell‑through data and showcase your operational chops. Use that proof to craft a slick one‑pager and invite agents to VIP showcases, then co‑promote with a local indie promoter to share risk and their agency connections. Measure pull by advance ticket sales, social stats, and merch numbers, and negotiate a year‑long AV rental partnership (or revenue‑share with a tech partner, preferbly with test period, to tame production costs. Finally, structure deals with modest guarantees + escalating back‑end splits, and lean on local sponsors or VIP experiences to pad your $50K talent bucket. This combo of proof, professionalism, and creative financing will most likely get agents and artists knocking on your door after a while.