postwhite
I recently updated my small mailserver and finally configured DKIM. But another change was easier and still had more impact: installing postwhite. This little tool takes a list of mail domains, then uses their SPF records to derive a list of their outgoing mail servers, then writes this list into a postscreen whitelist configuration. The current default setting contains 43 domains and generates a whitelist with nearly 2000 lines (each containing an IP or subnet). Everything is nicely scripted and can run as a nightly cronjob.
This setup eliminates my biggest problem with greylisting, which is Office356. Their combination of long email resubmit intervals and using multiple cluster servers for delivery attemps always lead to long delays before I received email from Microsoft or any company using Office356. (BTW, I really like greylisting but this is its biggest design problem: it works for single SMTP servers and enforces certain behaviour, but does not and can not consider clusters.)