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Personally I think it's the lack of success stories of having to use Web Monetization API. I don't mean success by getting rich, but if it can help people paying their bills and they tell more people about it I'm sure that's the turning point where Web Monetization can take off.
Also, there are lots of hecklers on the internet. Communities that have been a little bit on the toxic side will sometimes will try to push down things that they are not used to. By my experience this kind of situation will be very hard to convince people in because we just don't have enough "real life proof" yet that Web Monetization can be useful to creators--especially to the type of people who thought crypto is not a scam and anything that spawn out of it 100% is sham.
As for the second obstacle I think is the reach--which I also think is solvable as WM land is getting more mature as the time goes by. What I mean is, currently, we have 2 digital wallets that support receiving Web Monetization payments--which makes some KYC procedure very hard or simply not available in a few countries. Which is a shame, because even $50/month payments from Web Monetization can be very helpful for people living in developing countries, where content creating related jobs or gigs are simply out of reach by many.
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