Several options
There are many ways to handle this. It depends a lot on perspective. I too use the add-in so I can give you a feel for how I do things.
Most of my activity is project related so I will have a project item (Outlook Task flagged by the add-in as a project) and then the next actions items (outlook tasks categorized as Next Actions) and potentially additional parts of the project plan (outlook task items categorized as someday/maybe actions) for the project.
I keep project related notes and future actions in the body of the Project item in Outlook so it sync's with my palm.
From a strict GTD sense, you should only enter the actual next action(s) for each project as items in outlook.
Since the add-in handles e-mail fairly well, and since I get tons of e-mail, if I get something related to a project that is really a someday maybe then I go ahead and create a someday/maybe item for that project. I don't go out of my way to create someday/maybe's as items unless there is incoming e-mail for it. If there's something I know I'll need to do I just put that in the project items notes field with the rest of the plan.
It sounds like you're using word files for the project plan and there is certainly nothing wrong with that. I use the notes field of the project since I sync with a palm. If you only use outlook and don't have to sync with a PDA word is great. You might want to put a link from the project item in the notes field to your word file.
Your assessment on the weekly review process is mostly correct. I do exactly as you describe during the weekly review. However, I wouldn't limit myself to just the weekly review on a project. When I'm working on a Next Action for a project, I review the project plan as I complete one next action to see if I can identify the next one and if there's time available keep momentum flowing on the project and crank out the next couple of things I could do on that project. If I'm pressed for time, I'll go ahead and check off the next action I just completed, and make sure I have the next "Next Action" identified and entered into the list.
One thing I've found helpful is to create a "single project view" This takes a little in depth understanding of outlook views but I find it really helps me stay focused on a project:
1. Select the tasks folder and from the view drop down select Active Tasks by Project (GTD). From the main outlook menu select View; Arrange By; Current View; Define Views.
2. This brings up the Custom View Organize Dialogue. Copy the current view. Name the copy @Ad Hoc Active Task by Project and click OK.
3. You might also want to select View; Reading Pane; Bottom.
4. Right click in the task list area and select Customize Current View. Select Filter, Advanced, Field, User Defined Field in Folder and then Project. Set the Condition to "is (exactly)" and Value to your Project name. Click OK and in the task list select the project item (the task item with the project name as a subject) it should be displayed in bold.
Now you should have a task view of all the tasks related to the project that are outlook items, and below it a view of whats in the note section of the project item. You can quickly add new next actions with the Next Action button on the GTD Menu Bar.
You'll have to manually edit the task list in the project.
Also each time you want to look at a different project, you'll need to repeat step 4. Unfortunately writing the VB code to step through this is still on my someday/maybe list...
Hope this helps.
