In my case, I would kinda sorta _like_ to be able to apply more than one context to a task, but I have yet to find a sitution where the lack of that ability genuinely inconveniences me. So if the answer really is, "No, that would be too expensive and you wouldn't get any other features for eighteen months," that answer would be fine with me. No multiple contexts. I'll be fine. There are features that I want much, much more.
I suppose the situation where I would most like multiple contexts is the "shopping list" scenario. For example, to use a simple personal Next Action, right now I need a hook closure for a skirt. There are six convenient stores that might have one, and one less convenient and generally unpleasant and icky store that certainly will.
It would be handy if I could walk into my handy knitting store and check a context or perspective that shows all of the things that might be bought there (the hook closure, a button that I need for another garment, a copy of Threads) and none of the things that I'm absolutely not going to find there (butter, fire starters, my dry cleaning.)
But when I enter "buy skirt hook closure" as an action am I *really* going to go through all of my "store" contexts and add all of the possibly relevant ones, one by one by one? Or am I instead going to create a Crafty Store context and put the item there, and if I see an entry for yarn while I'm in the bead shop, so be it? If I'm going to do that, then I don't need the multiple contexts.
Now, if I want to have both the Crafty Store context AND the Icky Store context, because I'd be extra anoyed if I went all the way to Icky Store and forgot the hook, OmniFocus already supports that--I create a Crafty Stores context and make Icky Store a subcontext. I apply Icky Store, and that will make the item also show up when I'm looking at the more general Crafty Stores. This does mean that I have to remember to check the Icky Store context, specifically, when I'm there, to make sure I'm not distracted by other items. But I think that the multiple-context request assumes that we're checking the specific context; I assume that's the point.
But now let's imagine that I sew for a living and that I get to The City once a quarter to buy supplies, hundreds of items, and if I miss anything or run out of time I pay a premium to have items shipped. Imagine that I pre-research everything--I can get THOSE buttons at any one of those four places, and THOSE patterns at any one of three other places, and so on. Imagine that I really want clear-cut lists that show exactly who has what.
If I do that, then I'm probably going to just buy some sort of app optimized specifically for that, and take all that out of OmniFocus, and probably nag whoever writes that app to provide some sort of "shopping trip analysis" that tells me that I can get ninety-three percent of my items by going to these three stores, as opposed to ninety-eight percent of them by going to eighteen different stores, but that the first option will cost me thirty percent more for the items that the two options have in common. I could check off or eliminate items and it could optimize my shopping agenda on the fly. I like it! Somebody write it?
Anyway. This is similar to the fact that my bug list for programming doesn't live in OmniFocus, but instead in a separate database that I treat as project support material, because there are just too many fields that OmniFocus doesn't offer--and shouldn't offer; it's not a bug tracking system. Or the fact that some people are going to use contact manager apps even though they also use OmniFocus. For me, there's a level of complexity where the data exits OmniFocus and becomes Project Support Material. And that may be a philosophical conflict, re how one uses OmniFocus.
In my professional-sewing-shopping scenario above, OmniFocus would Next Action me through entering and organizing everything into the shopping app, and through making my travel and lodging plans, and throw a tickler to remind me to check whether ButtonsNThings is going to have their usual January sale, and remind me to follow up with the employee that I delegated to double-check the prices in the shopping app and to confirm that my wholesale buyer paperwork is still good, and tell me to inventory and double-check each day's shopping each night, and so on. It just doesn't handle the nitty-gritty of two gross of semi-translucent white shirt buttons; the shopping list app does that.
So I can't find a situation, for me, where I need multiple contexts that (1) don't already have a hierarchical relationship and (2) aren't so complicated that I want a task-specific app anyway. I struggle to find a situation where they would even really be useful. If Omni Group really does mean "it's too complicated to program/support" rather than "It would be wrong", well, I might want them to be more straightforward, but I still support that decision.