OmniFocus, Outliner, Plan, methodology for use
 

If you have OmniFocus, OmniPlan, and OmniOutliner and you are starting off on a fresh project which package would you start with first? And how would all three work together?

Assuming the project is of a large enough scope to merit doing so, brainstorm in OmniOutliner, build the overall plan/schedule in OmniPlan, use OmniFocus to execute the tasks.

You can open an OmniOutliner file in OmniPlan, though the changes you make in OmniPlan will not propagate back. Carrying the tasks over to OmniFocus is a bit trickier. For one thing, OmniFocus doesn't understand the full set of dependencies used by OmniPlan: Start->Start, Start->Finish, Finish->Start, Finish->Finish. OmniPlan also doesn't directly export to OmniFocus. You can use OmniOutliner as an intermediate file format that both understand, but OmniFocus misinterprets duration values when you import the file, though the outline structure will be correct. There's a lot of room for improvement here, but the good news is that the elves have apparently been hard at work on those improvements!

So OmniOutliner could be thought of as an 'Concept Manual' which can change but is referenced for direction.

Yeah, sounds like a good way to put it. Discussion of decisions made, analysis, etc. probably wouldn't find a good home in the project plan itself, but are still likely to be valuable reference materials. OmniPlan will allow you to link a document to the project plan document, and you could also link the OO and OP documents to the OmniFocus project. I would recommend linking rather than embedding, especially for documents that may need to change, like updating completion status for the OmniPlan doc.

For what it is worth, I'd use a mindmapping app like Novamind for all brainstorming and preplanning. It's a lot more fluid to maintain during the initial stages of any project. It will also export to OPML which plugs in nicely to OmniFocus.

My typical workflow is this:

. State Purpose as Central Node in Novamind
. Branch for Goals
. Seed Nodes for brainstorming (I use Lateral Thinking for brainstorming)
. Processing & Declaration of Concepts
. Next Steps Defined in a new MindMap Tab
. Export Next Steps to OPML
. Import to OmniFocus
. Process
. Review
. Do.

My projects are never of a scale where I need to use OmniPlan...plus I work with PM's who use OP so I don't really need to spend time in it.