This for me is the deal breaker. I say this as a sysadmin.
It's all well and good running a single server but if that shits the bed then you have to deal with it immediately.
So to run something that doesn't require 24/7 support I now have to run a cluster of servers.
I'll also need something to manage those servers like salt/ansible/puppet
I also need to deal with being my IP blacklisted because of a previous owner, or just entire domains now delivering my email because they don't like the fact i'm not using $email provider
Then there is spam filtering and the constant battle that is.
Or I could just pay someone a couple of bucks a month to worry about all that shit and not worry about it.