Maybe just the standard anti-grief/spam plugins, essentials, iconomy, Lockette for the chests (can't remember if that comes with another plugin), Stargate is a nice plugin for getting around the world quicker (works w/iconomy i believe). Like Gizmo said, it's ultimately up to Stylez on all that. All we can do is give suggestions.
Edit: Was just thinking, later down the road if all is going well. Multiverse would be a nice addition for a Skylands world, maybe a port to an Industrialized server as well (for those with the mods of course). Some more food for thought