[FatalError]

This has been nagging me since the first day I started using OmniFocus and I think I have understood the principle of the GTD-workflow.

I disagree with whpalmer4 in this case. And I don't see, why it shouldn't be possible to have multiple contexts. It's rather simple coding to allow multiple contexts and have that as an on/off option for power-users. The users that want to stick to single context can have that by default. The power-users can switch on multiple contexts and then have the assigned task show up in several contexts.

Is there any good reason to not implement this functionality?

During the couple of years I've been using OF I keep running into this issue over and over.

Here's an example:
What if I want to help someone with something that can only be done at his place? In this case I'd like to assign a person as context because the item is related to this specific person and I need that person to proceed.

Next, I'd want to attach the town this person lives in. Maybe the task isn't a major task but a little task for which I still need to be at that persons house, then I'd need the city. So whenever I'm in that specific town, I could drop by and get the task done on my way out of that town.

Whenever I travel I'd love to have a look at my contexts and see if there's anything open to do in a certain town.

I am aware of the fact, that I can assign places to a person. But that is not usable for me, since I might have to meet the same person at various occasions and places, thus having one single place assigned to a person would cause great confusion.

Also I am aware of what whpalmer4 suggests: simply add one component of the multiple contexts into the task description, but the issue with that is, that as (already the OP pointed out) then things might fall through the grid when using contexts.

How do others deal with this? And again, why not make it possible as an option? No one would get hurt, imo.