Advice on server project (worldpainter)

At the risk of getting blasted, and feel free to do so, I'm hoping to avoid looking at a thousand places to find the answers I seek. And here they are.

I'm thinking about making a server that starts with

1. Worldpainter created map by me.
2. Fine touch editing with world edit
3. And eventually having some tekkit mods (or others)

Sometimes the specific versions of Minecraft or java or bukkit or vanilla and requirements can be quite frustrating. I'd be grateful is someone dropped some info about what route to take here. Thank you.

Edit: I should clarify. Are these three desires even possible to combine, and if so, which version?