Do users have to sign up to something in some way to give you feedback? Are you jacking their attention with a web page pop-up at uninstall time?

If a user is already unhappy about dealing with you (safe to assume, since they're uninstalling your product. Fair to say?). It might be worth filtering whatever trolling you'd receive from such a feedback mechanism if it's that important to you.

As a personal interest of mine, what part of that 200 non converting trial downloads used the program up to expiry vs opened once?

This is why metrics and analytics have become superstars lately. Why hope for your users to tell you, when the software can do it by itself?

Following the article's use case, the software could transmit the last dozen or so commands or actions performed by the user. In a simplistic scenario, how would you interpret it if 40% of your user's last commands are "Save"? Success, surely! How about "Undo"?

The art and magic, of course, are in figuring out valuable yet inexpensive metrics for your app, capturing that data when you have thousands or millions of users, and interpreting the meaning.

Metrics are great but they won't tell you the user passed on your software because you're missing width/height info on selection

Similarly it seems easy for metrics to mislead you into thinking the most important features for your app are the ones that get the most usage. It could easily be that some other features users would like far more but are currently hidden or poorly designed so that users are avoiding them

Metrics can't answer every specific question directly. But if you look at the kind of activities your lost users performed last, and find a surprising amount of, for example, "Select", "Undo", "Select", etc you will know you have a problem area.

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.

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.

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

Ever heard of web-based software?