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Item 1:

I have been toying around with a custom tag in the notes of omnifocus that could be used to denote that a comment should be added to Jira. You could mark something with a hashtag for example in the notes section of omnifocus, and I could send that as a comment to JIRA.

Item 2:

Right now, I am just pulling in all item assigned to you. So if the responsibility is changed to you, it should show up in Omnifocus.

Item 3:

It could definitely run just on your mac. You just need to have node installed. I would be a command line program but I could set it up to run as daemon as well so that you don't have to remember to run it. It could be set to run at a schedule of your choosing.