I don’t feel the need to be complete anonymous, like you. But I do know of a group of people, who made an arrangement for 1 person to pay for all services they use online. There’s no real trail to any other than the one person. It works quite well for them, and they pay this person in cash…
There’s a lot of cheap mail-hotels, and a domain name is not costly either. I pay maybe 10 $ a year for both, and the mail is completely mine. I use Thunderbird as my mail-client on both windows, linux and android. Never had an issue, it just works.
I think that the biggest issue for a lot of people is, that they have to spend a little money on it. They buy shoes for 100 $ without thinking much about it, but private communication they often want for free…
We all know that using youtube, it like trying to stay on the good side of a huge bully. I still can’t figure out why anyone would like to use it, and other similar sites.