Does Discourse Standard include a server or should I pay for one myself? Is there a way to contact a discourse.org rep who can help me with some questions?
The prices on Discourse pricing | Discourse - Civilized Discussion are for hosted, managed service. You don’t provide (or worry about a server).
There’s a sales email address on that page and in my experience they are very responsive — although since it’s the holidays it might be worth trying your luck on answers here. Not that I think they won’t respond, but, you might find answers more quickly and reduce their vacation-time work at the same time.
It includes everything. They have a few trial so you can see how it works.