Hot take alert! As an avid self-hoster, I'd like to hear why.
Personally, I self host because the benefits I receive simply aren't available anywhere else at the level of quality I've come to expect - Jellyfin is a great media player, it's free, and I don't want to switch. Pihole provides ad protection and privacy for my whole home network. It's also free. Homeassistant is amazing, and free. Etc etc.
> It's also free.
Only if you don't care about your time or if your media collection is tiny.
Don't get me wrong, I love my 20 TB hard drives full of Linux ISOs, but it's a hard sell on anyone who doesn't have 'dicking about with computers' as their hobby. Regular old piracy using torrents has been a easier sell in my experience, once you can get over the hurdle of getting someone familiar with using a torrent client and the relevant search bar. Popcorn Time back in the day made that hurdle trivial. Getting people to use Jellyfin isn't hard. Getting someone to be the family/friend group Jellyfin sysadmin is a significantly tougher sell.
Pihole and the like is an easier sell, since it can be mostly set and forget, but it's not free unless you already have a computer which isn't doing anything, and even if you do, that computer isn't guaranteed to be one which has near-zero running costs when you factor in electricity.
The same sorts of problems apply to most things you can self-host.