[mattwdelong]

Yikes. If you're paying around $200/month (Not sure if this it total, or for each service, making it $400/month), would it not be feasible to invest in a VPS at linode and run your own mail server? You could even hire a decent system admin to look after it, and still save a few hundred dollars a month.

[Uchikoma]

I've run a mail server for 5 years for a NGO. Running your own mail server is not as easy as running your own LAMP stack. The is SPAM, IMAP, bounces, ... and many more issues with running your own system. My Postfix is only redirecting to gmail accounts. If that works - fine, but that's probably not what a small non-tech-savy business needs.

[jaredstenquist]

In my case, we're VC backed, heads down working on product. I love rolling my own for most infrastructure, but when you get into managing groups, aliases, password changes, SPF, DKIM, Webmail etc... for 30+ people, it quickly becomes a major time suck. I strongly believe in spending reasonable money to outsource anything like this.

This of course assumes you aren't worried about Google/M$ reading every email and stealing your trade secrets...

Puts on tinfoil hat