I self-host entirely on a Dreamhost VPS, precisely because of the issues you mention. I'm fairly experienced with many of the more technical aspects, but Dreamhost is more diligent than I am, and they stay abreast of issues I'm unaware of. So I handle the app layer (Nextcloud, FreshRSS, Fossil, etc.) and they handle the OS, web server (Apache, PHP, etc.), and certs (through Lets Encrypt). This balance has worked really well for me. No affiliation, just a customer since 2004.
