I used to have a home static IP address and run OpenBSD. I used mail whitelisting because otherwise spam was a pain. It was still a pain, though, because I'd have to work out where I might get mail from to pre-whitelist it.

So I went for Gmail with my own domain. No more spam, no more hassles dealing with span.

And for running my own services? File sharing: Dropbox. VPN: Nothing to VPN to.

What's better about running your own? I just got sick of managing it. OpenBSD, Debian, whatever I used, just broke in new and exciting ways every time I applied updates, meaning I had to spend time managing stuff that I could just hand off to others - and get for free/cheap.

It's great learning by managing your own server[s], but after so long doing it, I wouldn't want to continue without being paid to.