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It's really a matter of perspective.

The bottom line, the Omni Group is a business and they have a need to sustain themselves. One of the reasons they've been able to do so for so many years is directly related to the fact their apps bring a ton of value to their users, who then become loyal and keep purchasing their products. They aren't cheap, but you get what you pay for. They wouldn't be around this long if their apps sold for 4.99 or continually offered free upgrades.

Take for instance the work a person does. You get paid to go to work. Let's say you're an office worker and have worked for the past 3 or 6 months on this important project. You complete the project and 2-3 months after completion, you get a new boss, who doesn't necessarily agree with the direction and wants you to make some modifications to your deliverable which will take you another 2 months. On top of all that, your boss wants you to do it off-hours, on your own time, without getting paid. You going to do it? Hell no.

It's really the same principal. So many individuals don't realize that the people at Omni Group put food on their plate and are able to live a decent living by charging for their apps. If they charged 4.99 and gave updates away for free, you probably wouldn't be seeing the quality you do.

Then again, if you're using an app like OmniFocus as a simple task manager, then I agree, repaying is a kick in the balls. But if you're using OmniFocus the way it was meant to be used, then the time and money you've saved (even after only a few months of use) will pay for the price of a new version ten fold.