Well let’s not have too much illusions here : self-hosted services won’t be as good quality as the centralized services like the google empire.
- The tech giant have armies of engineers and sysadmin which are paid with madness salaries and as a whole they don’t care about ethics.
- The FOSS community are mainly volunteers and a few of them have the chance to get paid - yet they try to care about ethics. In that context, the quality is obviously less good, because based on mostly free ressources / donations, and because ethics sometimes causes the UX to be more complicated
- Self-hosting is not a practice that is made easier by ISP or tech entities in general (e.g. hotmail might say "fuck you i’ll flag your emails as spam for no good reason)
- There will be quacks here and there because you have other things to do in your life than checking 24/7 that everything is running smoothly
If your server is down for 2h or even 12 or 24h hours and your family and friends are not happy with this, they should chill and relax and think about how technology makes them so angry about stupid stuff
Of course, if this happens over and over, that’s a real issue. But of course we work to try to make this not happen.
So your expectation should just be to get someting “decent” here and that if, for example, hotmail politic is shit and you users’ mail fall into spam, they’ll have to consider saying goodbye to hotmail. (Maybe you don’t want to self-host email, but that’s just an example of compromises that can be required).
In my example, you see that it’s not just about keeping your server running and running fast, and having backup, but there are various small quacks that can happen.
Think of self-hosting as managing your own garden and vegetables : you don’t do this because the vegetables will be better or cheaper or you’ll have more quantity. You do it for the ethics and you should be able to compromise that it won’t be “as good” and “as comfortable”.
So my point is that if you put too much pressure on “it should be perfect because it’s not just for me and i want people to be convinced” then it will fail. It will simply not be as fancy and smooth as mainstream evil services. In a perfect society, people would be able to get paid to work for free and ethical technology, but that’s not the case. Instead, you and your users should realize that tech giant and society a whole has taught us to be looking for the perfect, fancy, round, red and smooth tomatoes. And if it’s not perfectly round you should throw them to the trash and impatiently run to another shop! Which is the root of the crazy consumerist society we live in where everything is a waste if it’s not perfect
. But with patience and tolerance, you may realize that not-so-perfect vegetables are yummy anyway. But I digress 
Just take a few steps at a time, don’t invite all your friends and family to switch all their services from one day to the next. Migrate your stuff and habits incrementally, learn along the way, tweak stuff where need, and it shall be fine ¯\_(ツ)_/¯.