Sorry, I was a little unclear - the setup is easy, it's the maintenance that's annoying. (I've run mail servers in one way or another for ~15 years. I use Google Apps for my personal email now but still maintain some servers that do about 10,000 emails a day.)

Even if you have DKM/SPF setup, someone can decide to start spoofing email from your domain to send spam, especially if your domain has been around a while and is relatively clean. Since you don't send a lot of real mail, all of a sudden 99% of the email marked as coming from your domain is spam.

It's not always even obvious that you've been blacklisted; mails may simply be significantly delayed (AOL does this, I guess so they can check for similar messages to other users), etc.

This is an issue for email providers as well, but they have people on staff paid to deal with it.

Even if you only have to deal with this once every 2-3 years, that's still generally going to be worse than simply paying someone $5 a month for a managed email service, not to mention to you have to deal with backups, etc.