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There's no question that Omni's products involve an upfront outlay of more monetary units than many of the competing products. In return, you get a product which, if you take full advantage of the feature set, may well be a bargain in terms of value received. You also get excellent support by email, phone, and forum at no additional cost.

Could Omni rake in more revenue by selling more copies at a lower price? Probably. They could probably get more revenue selling crummy Windows software, too. As a privately held company, they are under no obligation to follow the course that delivers the maximum revenue. They've chosen to do what they enjoy, and deliver the best service to their customers that they can. Doubling the number of customers for 10% more revenue isn't really going to make anyone happy. If the current revenue/customer ratio is satisfactory, and the company is growing at a sustainable rate, why change?

Indeed, I think they are trying for a specific clientele, as you posit. The price tag is likely to dissuade casual users (and casual buyers!) and tend to select for those users who are going to be intensive, involved users. Frankly, if you're not an intensive user, there's probably something you can get for under $5 that will be all you need. That's not to say that all OmniFocus users have hundreds of projects and thousands of actions in their databases, because most probably don't. But if you think you might need a tool that could handle that, from what I've seen of the other competitors' products, OmniFocus is probably the right choice. If you have that kind of a workload, a tool that helps you manage it is going to be $40 well spent, and you'll be glad you spent it supporting a substantial company that will be there when you need support.