Here’s a blog post I published yesterday. I think people here will have views on it.
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I’d argue stickiness is a lot looser of a concept than the concreteness you’ve defined here. I would define stickiness in the broader sense as a tool or workflow providing the least amount of paper cuts for a person’s use cases. This works well for defining how a tool can become “unstuck” as well. It’s when you discover a new tool that has sufficiently less paper cuts or identifies paper cuts in your existing workflow that you were unaware of.
For me, what you’ve described is more of general areas to look out for finding these “paper cuts.”
It seems like it would be a fascinating experiment to self-report on paper cuts in one’s own workflow and use it as a metric for selecting (or not selecting) an alternative tool.
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Friction is a key consideration for me. The lower the friction, the more likely I am to adopt
A new software.
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I’m inclined to agree, especially in keeping on doing the thing.
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I agree. It’s - as Merlin says - a list, not everything. 
The classic examples of “coming unstuck” - mentioned in the post - are Evernote and Remember The Milk.
The latter got overtaken by OmniFocus. Because I wanted more sophistication - having proved to myself that task managers were useful.
The former didn’t really get replaced by an exact equivalent. I considered DevonThink but - at this point - I think I can get away with less, not more. Which is unusual for me.
Ah, a new metric, Paper Cut Minimization Factor (PCMF) - I like it.
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I really like these definitions — useful. Wound your post:
- Productivity: Get more done.
- Reliability: Do it with fewer errors than I would.
- Enhancement: Do things I couldn’t do.
- Automation: Take me out of the loop of doing the thing.
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