I cannot overstate the comfort I get from reading you say you use OmniOutliner every day.
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Many of us love the app, and I would acknowledge that the there is a substantial body of work gone into the app, to keep it up to date with ever changing operating systems, which seems like a moving target.
I would however like to see 1. tagging system e.g. like task paper or Omnifocus, and 2. row level control of checkboxes which are unfortunately global.
The last change that was useful to me were the filters, but the above would be the most bang for buck for me at least. May be you could consider that?
