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Omni doesn't really publish roadmaps, except in the most general of terms ("bring all of our apps to the iPad", "OmniFocus 2 will have a major revamp of the UI"). Instead, they put out new versions that are a mixture of most-requested features, bug fixes, and features that may not have been requested but that Omni feels will enhance the product. They do it on a sxhedule that is rarely shared with the outside world, because their iterative development style rarely leads to accurate estimates far in advance, and missed predictions just get the customers upset, whereas there is little appreciable upside for having gotten a prediction correct.

On the flip side, they are very responsive about fixing bugs, the support group is excellent, and the time between major versions is usually measured in years, so they aren't always asking for more money, and each major version has significant development done over its lifetime. I suspect that may be especially true for the iPad apps if Apple never provides a way to sell discounted major version upgrades.