That was a thought provoking article, thanks! I agree with much of that analysis for small amounts as he suggested, but for larger amounts I'm not sure. I think we can break tipping into two groups - passive tipping, where you tip someone for content they already produced like a blog, and interactive tipping, where you tip someone for a response they give you. I think the 2nd type has much more potential to generate meaningful income
@TPTB, you for example, could open a Q&A thread for tech & other advice. An answer that takes you a few minutes to write *might* be worth thousands to the questioner. That type of thing would probably fall under 'tipping' but it's different to a fractional penny, and if it was easier to do it might take off.
Problem is that maybe only the person who asks tips you and the rest just decide you've already been paid. The problem with that model is opportunity cost. I am not going to waste my time for $10 per Q&A answer, because my opportunity cost is potentially $millions (for myself, and $billions for society) and I answer for other reasons that pertain to me attaining that $millions goal.
The tipping idea may work as a replacement for an up vote for site such as StackOverflow (StackExchange) where there is ongoing competition to see who can receive the highest ranking. Here you are competing not for the money but for the reputation, which makes it worth while.