Gmail vs. Entourage vs. Apple Mail App - Tagging, Filtering, Persistent Searches

I've had Gmail accounts since it first launched. However I was still aggregating all of my email accounts into Entourage on my desktop. When I got an iPhone I switched to the Apple's Mail app. Seemed to make sense because it syncs directly to iPhone's mail app.

One of the things that I really like about Gmail is its tagging (labels) capability and the ability to tie those tags to automated filters for incoming messages. Granted, with a plug-in like MailTags you can do the same and maybe more with Apple's Mail. However, the main differentiator for me right now is that with Mail all of those advantages are only available on my desktop. If I'm in mobile mode it's just not availble to me.

I'm not done exploring the potential of  Mail, but for now I've decided to take the plunge and make Gmail my main email management app, with all accounts forwarding to one Gmail account. I haven't begun to uncover the full potential of Gmail, but a few things have started to emerge in the way I even think about organizing things.

With Entourage I pretty much used the hierarchical file system that we've all gotten used to, but that was always a bit frustrating when a message might benefit from multiple tags (not to mention that the search utility left something to desired. Mail.app was a huge improvement with the combo of filters, smart lists, and the tagging plug-in mentioned above. In the end though, all the advantages are realized on the desktop, and not available if I'm mobile (I also may not be enough of a geek to realize that there's a way to have my cake and eat it to).

As I've been reconfiguring things in Gmail I've found myself still thinking in terms of hierarchical categories, and assigning labels as if they're "folders" they way I'm used to. Little by little though I've been discovering that with the search operators that are available in Gmail's search utility, even tagging may be overkill in many cases. Once you understand how use these search operators, and combine them, it's a whole new ball game.

Then I stumbled across this post by Matt Cutts about a Greasemonkey script that augments Gmail with persistent searches. Wow! What it does is add this sidebar to your Gmail interface. You can construct complex search queries that meet multiple conditions and then assign filters to them. You just name it something simple, but what you end with is tagging on steroids.

Glad I ran across this while I was still relearning the paradigm.

Bottom line for me is that while it means I forego the convenient synching between Apple Mail and the iPhone. Just seems that I get a whole lot more just using Gmail via the iPhone's Safari browser.