My Gmail setup
Sometimes it's best to just start over. That's what I decided to do with my e-mail for Odyssey of the Mind. At the beginning of the season, I created an e-mail account on Gmail specifically for team communications. It has worked out very well.
I wanted to keep Odyssey e-mail separate from my business and other existing personal e-mail accounts simply so that nothing would get lost or overlooked. Gmail does a very good job of keeping notes organized by conversation, and sending e-mail to defined groups is ridiculously easy.
Here's how I set up my contacts. Each parent address is labeled with the parent's full name and the child's first name. For example "Joe and Sue Smith (Scott)". When I type either the last name or the first name of the child in the To field, matching addresses are suggested automatically, making communication about a specific child very easy.
All of the parents' addresses are in a group I called "OotM primary". They're also in a group I called "OotM Extended" which also includes other interested parties such as the sponsoring teacher at the school. Mail to all parents or all interested parties is as easy as starting to type "OotM" and choosing one of the suggested groups.
Notification of new mail
Ordinarily I find e-mail notification too distracting. But, sometimes messages are time-sensitive, and I've found that the volume of Odyssey mail I receive through my Gmail account is low enough that the interruptions from notification are OK. (By the way, I haven't mentioned yet that my Gmail account has been 100% spam-free!)
Google offers a Gmail Notifier for Windows, but unfortunately it is blocked through my employer's firewall. Being a certified geek, I found another solution. I already used a news reader to gather interesting stories from RSS feeds. It turns out that you can also turn your Gmail into an RSS feed (with a password required for access). I use FeedReader and subscribe to the feed https://gmail.google.com/gmail/feed/atom. Enter your user name and password into FeedReader when setting up the feed. (You can also try formatting the feed as https://username:firstname.lastname@example.org/gmail/feed/atom if your newsreader doesn't support passwords through its interface.)
The default notification window for Feedreader goes away after a while. If you're away from your computer when new mail comes in to your Gmail account, you might not see the notification. But, you can set the notification for your Gmail feed in Feedreader to have added importance. This makes the notification window "sticky" and it will remain displayed on your screen until you dismiss it. To do this, right-click the feed and select Edit smartfeed. In the pane that opens, select Show notification with added importance.
Preparing for next season
Gmail organizes your mail using labels. You can clean up your Inbox and prepare for next season by labeling and archiving your mail from this season. Google provides a tutorial on how to use labels in Gmail.