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After the experience of setting up my own mastodon instance, it's clear that we have a long way to go to make decentralized web services commonplace: As it is right now, it's not really possible to bring up your own instance without a high investment of money and knowledge. This already severly limits the type of people invited to run the "open web".
The appeal of centralized web services and apps is that it's very easy for anyone to get started because someone else is going to the trouble of setting it up and running it. For decentralization to become the norm we need access to be as easy as that.
Here's what I think is required:
1. It should not require a technical person to get started. Running decentralized services should be as easy as installing an app. This is why I like p2p approaches like We, they're very simple as a user even if internally it's complex.
2. It should not require deep pockets to get started. Ideally it should run well on old or low-spec hardware, and it should be available across platforms.
3. It should not require a huge moderation burden upfront. If I can get started with a few of my friends first and I can build a community from there, that's much better. My community and I should be able to control when / if this particular instance joins the general public.
4. It should allow for easy application development. Drag and drop for most cases, with the option to dive into code (i'm thinking of RPG Maker). Replicating services like twitter or youtube is thinking small. If you abstract away the plumbing and let more people build what they want, then we'll start seeing some apps that only decentralization can bring.
5. It should be free / libre.
I'm sure there's a lot more that goes into it, but I think without those it will never work. People have things to do and problems to solve and will solve them with the tools that they have at hand. I have a lot more faith that peer-to-peer service will achieve this than any of the client-server approaches.