[whpalmer4]

OF's iCal sync was built to allow people to get their data on to mobile devices before the iPhone was opened up to 3rd party development. Given the general GTD philosophy, it makes sense to map contexts into calendars. Otherwise, how are you going to look up every task assigned to a context?

Also, are you aware that OmniFocus actions are synced to the calendar as tasks, not as appointments? The general thinking is that the so-called "hard landscape" items such as appointments, meetings, etc. go directly on the calendar, not into OmniFocus, which manages all the work that you do between or around the stuff scheduled on the calendar.

I hate to say it, but it looks like you're trying to bash a 4-sided peg into a round hole... Roles aren't contexts. Roles are collections of projects. I don't understand why you want to subdivide your Errands context by role, as you seem to be doing in your example. Are you going to go to the office supplies store 3 different times for your 3 different businesses? No, you'll buy everything you need for all of your businesses on one trip (maybe in 3 separate transactions).

OF comes with a 30 day money back guarantee, so if you don't like it, you don't have to keep it. The link to the refund policy is at the bottom right hand corner of the online store, as I recall. But really, there's nothing you've mentioned about your situation that isn't true of many other people who successfully use OF and GTD. If the way you want to use the system and tools is too difficult, it won't work for long, and you'll just be wasting your time and effort adopting it. If the tool doesn't fit the intended use, you should reconsider the tool and the intended use. A cordless drill/screwdriver makes a lousy hammer, but boards can be fastened together with screws as well as nails...