PC Master Race

I can't answer why shoulderoforion feels that way about backups. But I can answer why I feel that way about email: Google is a bigger part of people's lives, and so is a more dangerous monopoly. Therefore, I pick Microsoft for email.

Tons of businesses have their email hosted by Microsoft or Google, and tons of individuals have their email hosted by Google. If you want to self-host email, as I used to do, you need to interoperate with both of them.

To send email to a Google-hosted domain, you have to jump through a series of increasingly obscure hoops. Not all at once -- they introduce new ones once every week or month. First, it will let your email through. Then you will get rejected with a URL for a new hoop. First, getting your IP address off a "policy block list", which is basically a preemptive spam filter for static IPs that have never sent any email. Next month, you have to do SPF. Next, DKIM. Next, you have to create a Google account, and do something with your domain while signed into that account. Next, your Google account gets banned without recourse, and you have to wait 3 months for it to be deleted to make another, and all your mail is rejected during that time.

To send email to a Microsoft a hosted domain, you have to first send email to that person, get shadowbanned by the server, verify that your mail did not end up in their inbox, nor junk directory, and then call them and ask to be whitelisted. Depending on the circumstances, you may need to do this for each domain you send to, or each email address. The method of whitelisting varies, because the error message varies. If you can't contact a postmaster at the company, get fucked.

This is absolute monopolization. The only way to play the game is with their rented game pieces. So you have to pick one, and you pick whichever one is less dangerous.