In the summer of 2011 I, at the insistence of my older brother, installed Debian on a partition on my hard drive. At first I was a fan purely due to to the better boot times, and the more practical layout. But as time went on I noticed a few issues.
Since I didn’t really know what I was doing, my brother acted, and still acts, as my sysadmin. He remotely will update Debian whenever we both happen to be online at the same time. I’m hoping that by the end of the class I will be able to do most of that myself, and only utilize him for major issues or things that I don’t actually understand.
Another issue is that, even using Wine, I can’t play several games that I enjoy. Therefore, I can never permanently switch to just using Debian, until it is able to support those games.
Debian also uses Icedove as an email client. Although the initial set up was a little more confusing, it works better than Outlook, except that it can’t see what I do on my Windows partition, which makes the crossover difficult, since most of my data is stored in Outlook. I have the same issue with Iceweasel and Firefox. I tend to just leave tabs up, so when I switch Operating Systems, I don’t remember what I had up on the other and what I need up.
On the whole, I prefer Debian to Windows, but I just need to learn Debian better before I can make any kind of major switch.
I’ve found that what works for me as far as synchronizing data across OSes (and across machines) is using “cloud” services whenever possible. In addition to the obvious contenders like gmail for mail, the Google Chrome browser has a nice sync feature that allows you to synchronize settings, bookmarks and even open tabs across devices (for all intents and purposes, two OSes dual booted on a single machine can be thought of as two separate devices). If you do want to use a local email client, instead of a webmail interface, be sure to tell your client to connect to the mail server via the IMAP protocol instead of POP. IMAP keeps the data on the server, making it possible to synchronize across multiple devices (though I don’t know if that applies to everything Outlook does).