I manage computers and networks for various businesses in Hawaii. I'm familiar with Windows & Linux Server Operating Systems, Tape and Tapeless Backup, Computer hardware, networking, etc. I tend to emphasize training and documentation.
I've successfully migrated several clients to Google Apps Email. Google mail is very reliable and can even sync with Outlook which is very important for users who can't get used to web interfaces. Outlook sync is available for Education, Non-profit and Premier Editions. Premier edition costs $50 per user per year. I've had a client go from 200+ spam messages to a couple messages per day after going with Google Mail.
I've also introduced several clients to Dropbox. It syncs your files on all your computers (Windows, OS X, Linux) and it works more transparently than Google Docs. You can continue to work normally with your favorite word processor and access your files in the usual manner. They give 2 GBs free and 50 GBs for $99 a year.
Additionally you can access your files from Dropbox.com when you're using someone else's computer. Just log in with your username and password and voila, there are your files. Arguably the best feature is your files are already backed up. You can restore to a previous version easily through the same web interface. You should still backup your files elsewhere — you can never be too careful.