+1 for self-hosting. Doing that for nearly 10 years now, by far the most difficult part is setting up a mail server, but after that you can put on your resume that you know how to configure Postfix (which I am quite certain is one of the most difficult Linux server applications to configure). Backups, webmail, file storage, calendar etc. are quite easy to set up.
Postfix has flexible configuration system with many knobs. I would say though, that official documentation is nice and detailed. Last time I checked Debian defaults looked pretty good, so you don't need fiddle too much to get reasonably useful and secure setup.
