With extensive usage, I have slowly become less enthusiastic about OmniFocus than I once was. It’s generally an amazing piece of software. However, it is also extremely complex, and I don’t mean in a power-user kind of way: I mean in a confusing way. No matter how well I learn the software, I still “lose” my data. There are so many ways to sort and view and filter your data that it is also amazingly difficult to find things. I’ve seen this problem discussed ad infinitum on the Omni forums. It’s such a serious flaw that I would never recommend the software, despite its other virtues. This app is a power tool for geeks in love with GTD.

Syncing with the iPhone application was so consistently error-prone over several months of experimentation that I eventually gave up.

OmniFocus support, generally excellent in my experience over the years, was not exactly perfect either. Ultimately they dropped the ball, offering to examine my database for the cause of my chronic syncing problems, but then taking much too long to follow-up (weeks).