I've set 25-user at $112 and 50-user at $225 for a specific reason. Atlassian pays us add-on vendors monthly, but only once we've done $666.67 in sales since the previous remittance.

Atlassian dictates the maintenance renewal price: 50% of initial price for customer to extend maintenance by 1-year.

I've only been at this 1-year, so I don't know what the renewal scene is like. But I suspect renewals are good in this market, since enterprise customers often have policy requiring all their software be supported.