usertech, I watched your video and I have read through most of this thread. I have a few questions about your particular workflow; admittedly workflows are specific in that each of us find tools and techniques which allow us to perform actions more effectively.
1) What is your planning and execution process when using OmniFocus?
For myself, I plan my projects in planning mode and execute my project's tasks via context mode through specialized prospectives. With this being said, ideas do occur when not in planning mode. In these scenarios I use quick entry and/or if necessary I switch to planning mode to make an adjustment to a project.
2) How many project/tasks do you have?
Part of project management is, as you say, choosing from a list of actions/tasks to complete an move projects forward. However, it is also part of project management to know when to limit the amount of tasks you can handle.
3) Related to #2 are you using start dates and custom perspectives in OmniFocus to limit the items in you context view?
Priority is given to calendar items which can only be completed on a specific day, a firm due date, or conversely those not starting until a later date are not shown. These variables allow for an automated filtering by their importance. OmniFocus gives users the ability to create specialized perspectives and assign start dates in order to better limit the number of items in any given context list. For instance I can be at work and only see work related tasks and only those that are available to me for completion.
OmniFocus gives the user the ability to filter projects by using custom perspectives, limit visibility through assigning start dates, highlighting due tasks, and a catch all flagging option. I have not found a situation where I would have more than a reasonably small list which I could quickly scan and choose a task to complete in any particular context.
Now, I understand everyone has a workflow preference and I did find difficulties when I first approached GTD. I would suggest you continue to find elements which work for you, but consider many of the users here have worked with the software for a longer time than myself and possible you. There are many resources where I have found solutions to many problems I have had with managing projects.
I have two final offerings.
A) Your desire seems to echo the old mantra of assigning priorities to tasks which GTD was a solution for. If I remember correctly this is addressed within the first ten pages of David Allen's book Getting Things Done. The example of your shopping list route does not address potential changes in priorities -- after planing out and manually sorting all your store locations and beginning your errands you get a call and you need to pick up an item immediately at the store which is in the middle of your route; now what? Reorder your tasks? Plan the execution of the route again including the new information?... but IMMEDIATELY does not allow for this. Smaller scannable lists do allow for this type of flexibility.
B) To assist in your desire to have a specifically ordered list for shopping I have a resource for you to research. My prompt to search for this was that I needed to manage a grocery list from OmniFocus and share it with my wife who I can sometimes get to use the Reminders.app on the iPhone.
These are a set of three AppleScripts I found which send tasks to the Reminders.app and can sync task completion back to OmniFocus. I use it with a shared grocery list with my wife. Take what you will from these and I hope they help with your workflow.
https://github.com/ChewingPencils/om...s-to-reminders
In all your desire to have a specific list of priorities top to bottom is something I have needed to address personally as well. Contexts are flexible for a reason. This reason for me was when I realized life is also every changing and flexible as well and I could not make concrete plans which could stand against this level of unknown possibilities.