I've been self hosting for nearly 10 years now, and in all this time the biggest pain point I remember is setting up OpenLDAP. That's why I created LLDAP (https://github.com/nitnelave/lldap), a minimalistic LDAP server with a nice web interface that is very easy to set up and configure. It needs a little bit more love before the 1.0 release, but it's already very usable.