I've made a start-up that has really tried making micropayments work (blink.net) and I know there have been many other attempts.
Some of the pain points can always be addressed, as it's just implementation difficulty (having an auto-pay system when opening and article, and actually being able to get a refund within a short time window if the title was clickbait -- with some limitations of course).
The main problems that always remained were:
- the dificutly in convincing a user to actually pay, which was a psichological barrier. People also don't understand that many articles would have to be priced at 20-50 cents, even more, to be worth it, or there should be an issue pass with the actual price of the whole issue.
- the publishing industry being a mess, hard to coordinate as everyone wants to do their own thing, and early experiments failing, ruining the reputation of the idea itself. Many people say micropayments are something that needs a good time, but nobody knows when that time will come.
- the huge fees that processors take (2% + 29 cents), meaning we needed to load into a wallet a minimum of 5$. After learning all the tricks of the industry, I felt a need to throw rotten tomatoes at whoever thinks that cashback should be legal.
The combination always made it a horrible problem, and at this point I'm even considering making the existing project a non-profit, if that might get something off the ground, but now it's just in low-maintenance mode.
This is just off the cuff, but I could go for something sort of like a 'daily paper' deal where I get debited a couple bucks for access to the news papers site for a day, or maybe even just the materials published that day, but that sort of seems more complicated to implement.
Then, if I'm reading it so often that it would be more cost effective to just subscribe they can start pinging me about it.
We have that implemented, it's just that nobody wanted it. Our pitch basically was that "Why can you buy today's paper on the stand, but can't do the same digitally?" Turn out the answer is complicated.