My Outlook set up
Joey:
Because of the fundamental change Lookout has made in my approach to using Outlook, I really don't bother much with artifice like "contacts as projects" or other ways of overcoming the inherent lack of support for Project and Context in Outlook.
This is a long post (you have been warned

)
In a nutshell, here's my current system:
E-Mail
I have a Current Projects folder at the top level of my primary Outlook account (my work e-mail - not the default Outlook profile because my company uses an IMAP server). In that folder, I create a new folder for each project I'm actively working on.
I also have a !Today, @Action, and @Read/Review folder at the top level. I use Today! for stuff I have to deal with today but that will take longer than 2 minutes. I
never leave the office without clearing this folder. @Action is for stuff I have to take action on but that does not necessarily require
immediate action. This folder is always emptied as part of my Weekly Review. @Read/Review is for newsletters, promotional offers, and reference stuff that I want to read more thoroughly and/or file for reference. I review this folder weekly and
nothing stays more than two weeks... period! As DA has pointed out on more than once occasion, the danger in a Read/Review folder (digital or analog) is that it can quickly become a black hole. :wink:
As e-mail arrives, I do the Two-Minute Rule thing and
Do It (reply or act on the message in some other fashion),
Defer It (drag it to the Task icon and make an actionable task out of it - the e-mail than goes into an appropriate folder), or
Delegate It (forward the message to my assistant, my wife, my boss, etc.). I've become almost vicious about e-mail and much of what I use to save now gets deleted as soon as I've read it.
Part of the reason I can get away with this ruthlessness is that I have adopted a tool called ContentSaver which allows me to capture web pages for future reference. It uses folders and categories and I have them set up to mirror my Outlook setup. Much of the mail I used to store was retained because it had URLs I thought I'd want to follow up on. Now I just grab the page instead. A reference to the page goes into my Project task (see below).
For finding things, I rely on Lookout's amazing speed and flexible search capabilities. I have yet to fail when searching for anything. I can always remember at least two things about the e-mail (or other Outlook object I'm looking for): a person's name and one or more keywords related to the project/action/outcome. Generally I also have at least a rough idea of when the item was received or sent.
So I drop e-mails into current project folders or reference folders in my Outlook hierarchy and find them using Lookout as the need arises. I have pruned my Outlook folder hierarchy to no more than three levels deep (used to be five!) and am working toward a two-level hierarchy as a goal.
Tasks
I have categories set up for all of the @XXX contexts as well as secondary categories that map to my key result areas at work and home. I tag everything (e-mail, tasks, appointments, and notes) with at least one, but generally two categories. I have constructed a custom view in Outlook that groups by category and sorts by due date date, then subject with a filter of "Complete: not".
I make heavy use of the notes field in Outlook's tasks. When I create a new Project task, I list as many of the next actions that immediately come to mind that I can in the notes field as well as links to any reference material I might have related to that project. Project tasks are never dated.
I create Next Action tasks as I review my Project tasks (I do a daily, first-thing review every morning). Sometimes I cut-and-paste from the NA list in my Project tasks, other times I generate a next action task more spontaneously. I
do not get hung up on trying to list every action for every project in the Project task note field. It's just a bucket for ideas and reference information.
Calendar
Not too much special here. I use one or two categories (as mentioned above) and always associate one or more contacts with an appointment. Because I use Outlook's Journal feature for a small number of folks I interact with all of the time, I can use the Journal records as another way of looking at my progress, relative to another person. Of course Lookout indexes all of the Journal entries as well. I looked at the Outlook Business Contact Manager add-in but did not like the bifurcated contact list it imposes and I'm not especially sales-oriented so it felt too "structured" for my needs. Journal works fine for me.
Again, I can find any appointment using Lookout.
One technique I have developed to dance around the whole "hard landscape" issue is to make an all-day event in Outlook for thing I really want to, but don't have to, accomplish on a given day. They don't take up time on my schedule and can easily be carried forward if they don't get addressed. I rarely slip an item more than once because I try to be judicious about putting anything on the calendar unless there's a very good likelihood it'll get done that day.
Notes
Outlook's Notes are awful. No other way to put it. I don't use them much - they're primarily a way to get information from my PDA to Outlook or to have a portable version of Outlook info to take along on the handheld. I do almost all of my note-taking in OneNote. I'm looking forward to the SP1 of OneNote as it will integrate better with Outlook than the initial release. I understand that the forthcoming release of GoBinder also has Outlook sync so I may look at that as it has the Agilix eBinder technology that lets you "print" anything to your notebook and annotate it using the Tablet PC's ink and highlighters.
Whew! Probably more information than you needed but there you have it. Of course I use a number of other tools extensively in my total workflow. Mindjet MindManager is the "third leg" in my GTD "stool" along with Outlook and OneNote, for example.
Hope that helps.
--Marc