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Originally Posted by nielkfj View Post
I bought a mac after 20 years of Windows and DOS. ...
Welcome! You have an adventure ahead for sure.

Originally Posted by nielkfj View Post
... I guess these primary categories would be the equivalent of contexts in OmniFocus. However, I also have a few 'secondary' categories, which I use to identify some tasks within the 'primary' categories. So then I have the ability to search on a secondary category name to see only those tasks belonging (i.e.: tagged)*to*the secondary category.
This is a reasonable starting point. You can make sub-contexts in Omnifocus. For example, my set up has the equivalent of this break down in a top-level context Waiting For ...

* Waiting For
-- Work
--- Colleague
--- Staff
-- Personal
--- Spouse
--- Child 1

Originally Posted by nielkfj View Post
... Outlook doesn't have the ability to make sub-tasks, so I am looking (finally) for something with more functionality, even though I could simply buy the OS X version of Office and save myself the the trouble of all this research.
Yes. And you could also buy yourself a skateboard and use it to travel around the US continent. But, that would be a rather foolish thing when other tools are available to do the job so much better.

Omnifocus can group sub-tasks as sequential (one after the other) or parallel (any one at any time). This is an often over-whelming yet hugely powerful feature.

Originally Posted by nielkfj View Post
Many years ago I attended a half day seminar about work productivity. ... I remember they talked about dividing tasks into a four quadrant system ...

1) Important - Long time to complete
2) Important - Short time to complete
3) Not important - Short time to complete
4) Not important - Long time to complete

This is not really GTD. This is more like the priorities of the Seven Habits religion. It uses two classifications (Urgent, Important) and creates a four quadrant matrix (U + I, I, U, neither U nor I).

The zealots of GTD might argue, such an approach is heresy or worse.

Originally Posted by nielkfj View Post
... long presentation of Outlook method cut ...
Originally Posted by nielkfj View Post
Ok, so this is essentially how I have been organizing tasks for the last ten years. If I was to follow the GTD method, can you tell me how I would be organizing my tasks differently? ...
First, you should organize in Omnifocus in a way that is comfortable for you. Secondly, you should prepare now that you will likely re-organize things in Omnifocus a few times until you find what it is that really is comfortable for you. Thirdly, you might try hard to avoid at first that you play with your new tool while you try to fit everything in to it.

With this in mind, I recommend that you pick a few key Projects to develop within Omnifocus. Avoid that you get frustrated when everything does not fall in to place right away, and also avoid that you absolutely have to have everything fall in to place right away. Have a back-up system, such as a pen and paper and calendar, that you know how to use.

Finally, I recommend the Websites

to give far greater detail than could ever be put here.

Best regards in you new adventure!