I’ve always hosted all of my email on my own servers just to save money. > I will switch from self-hosting my email to $2.99/month email accounts at Rackspace.

I think this is really smart, assuming Rackspace does a good job of delivering mail. I don't think self-hosting email ever makes sense from a cost savings perspective.

What is you're time worth? A single hiccup and you've blown base $3 per month or heck $50 per month in cost savings.

I currently point the MX records of all my domains to my existing Fastmail account.