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On the other hand, who wants their drawing software to track their every movement?

This is hugely important. Any analytics had better be opt-in from a very visible and honest request dialog. Otherwise, quite frankly, it's unethical.

And then you lose users on that request dialog...

How do you feel about properly anonymous opt out logging?

My feeling is that anything personal including user content and searches should be opt-in but opt out is ok for monitoring feature usage that can't be linked to an individual. Obviously online/web apps reveal at least this anyway. Does context web/mobile app/PC app make a difference?

My perspective is that you are using that person's processor time, so it's okay to have anonymous opt-out if they know what is happening, otherwise I don't think it's appropriate.

Ever heard of web-based software?

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