I can’t help thinking that coarsely segregating customers into plans and overly streamlining the sign-up process might not be the optimal choice in your case. Why not just drive everyone to contact sales directly like, for example, landing page for Ellington CMS does[0]?
You can still market a cheap newcomer plan with low specs, limited support and only basic customizability, strongly implying that it’s the choice for young poor bands. Anyone above that is probably better off working with you directly so that you can estimate the costs and price the solution for them individually. Your highest plan is €199/month—would you bill Metallica that much if they come?
[0] http://www.ellingtoncms.com/cms/, a CMS originally built for small-ish newspapers, also where Django framework was born.
