About two years ago, I lost some saved emails using T-bird, and I decided to look carefully at what I was doing and what I could to ensure that didn’t happen again. I saw that 99% of the time when I am composing messages, I am sitting online, usually in my office, or someplace else where I have a Net connection. I had heard about Gmail and took a look and was immediately hooked. There were four things that motivated to switch over (and these might not be as important to you as they were for me):

First, I don’t have to worry about saving and storage of messages Google does it for me. And as their mailbox keeps getting bigger faster than I need, it is limitless as far as I am concerned. Now others may have run up against this limit, and now Yahoo email is truly infinite, but I hate their UI. I think I have about 2 of GB of mail, and as I mentioned in my post Gmail is above 7 GB and adding more every day. At the time, they didn’t have IMAP, but now that they do it makes for some choices here.

Second, they did a great job with labels, making it very flexible to store messages in multiple buckets. The latest versions of Outlook also do this, and I haven’t checked the Mac, Vista, and T-bird versions lately but at the time I switched they didn’t do as good a job. If you do use IMAP and have lots of labelled messages, you will find this vexing however.

Third, I use multiple machines, both PC and Mac, and having all my email and contacts in the Gmail cloud is a real plus for me. I don’t miss having local email on my desktop at all.

Finally, they did a great job with groups of contacts, and making it easy to organize my contacts is really at the heart of what I do with my email. I can have one contact as a member of multiple groups, to make it easier to find and communicate with people. Again, the newer versions of many email programs all support this, but at the time I was switching this wasn’t the case. I usually have two windows open in my browser at all times the Mail and Contacts windows.

There are some issues with Gmail, however, not enough to make me switch at this point. First, the numerous outages over the past few weeks that is troubling. Second, the latest UI doesn’t work with the large volume of contacts and the many groups of them that I have I still have to run the older UI, luckily they have a switch to “older version” that I use. And exporting your contacts doesn’t export the groupings, so once again I am captive to Gmail until I can figure this out.

Since I switched Gmail supports now both POP and IMAP access to their mail store, and there are programs like Cemaphore.com’s MailShadow for Google Apps that can synchronize an Outlook/Exchange account with a Gmail one. That makes the line between online/cloud email and local email more blurred. It all comes down to what UI you like, and where you want to keep your contacts, and how much offline composition and contact lookup you do: in my case, very little, and these days just about everywhere I go I can find a connection.

The other thing going for Google is that Google Apps is free to host your email for your domain, so you have the best of both worlds — you have the large online storage, the Gmail UI, and your own domain dot com — plus I think up to 100 mailboxes — all for free. It used to take a few days to get this going, but last week it took about an hour to setup, switch my MX records, and I was good to go. I don’t see why anyone would want to host their emails anywhere else.

Of course, this gives me a single point of failure with Google now, so I might keep that Yahoo email box around a bit longer :-).