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I love incredibly through guides for things I will never do :marseywhirlyhat:

I think the biggest obstacle for selfhosting is actually email. My experience is that most providers just won't deliver your shit without even telling you why. The spam problem is so vast any domain/IP with no reputation (read: not paying AWS SES, Gsuite, or a managed host) gets blocked with no appeal. And ironically email is one of the most valuable things to self-host, since so much of your digital identity is tied to various emails and losing access to one basically means losing all possibility of recovering those accounts.

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E-mail is important but the actual server is not as important as you'd think. If you use your own domain name, you control your e-mail address even if you use a hosted webmail provider. You can download your messages locally with IMAP to have any old messages if the provider goes out, and just change your MX entries for your domain to a new webmail provider.

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