I've been working on my to-do list lately, and I figure I'll share it. I'll also post it below, as well as keep the list in the top post of the thread. Let me know your wishes, and I'll probably add them to the list.
So far, the list is pretty short:
Phase 1:
Install & open server
Test server config
Phase 2:
Can into Spigot/Bukkit
Edit & test server config

Investigate user permissions & commands

Investigate plugins [[ IN PROGRESS ]]

- - Find & install a town p.i. [[ IN PROGRESS ] ]

- - Test & configure town p.i.

- - Find & install economy p.i. [[ IN PROGRESS ]]

- - Test & configure economy p.i.

- - Find & install NPCs p.i.

- - Test & configure NPCs p.i.

- - Find & install multi-world p.i.
Install & configure dynmap

Test dynmap [[ IN PROGRESS ]]

Anti-xray (anti-cheat? surely no one
here wants to be perma-banned)
Phase 3:

???

World painter thing

Acquire standalone server hardware

Super Cool Spawn Location!

Live public launch? [tentative]
Phase 4:
Profit!
As you can see, we probably have a good couple months (at least, at my current schedule) before I'd feel comfortable moving into a "phase 3" thing. In the meantime, let's have some fun.