I upgraded my main computer (a recent-vintage iMac) to Mac OS X.7 “Lion” yesterday morning. Everything went smoothly. One of the many advantages of Lion is a much-improved Mail app.  This has led me to give some thought about how I get and send email. I can’t say that I’ve made a final decision yet but I’m writing just to share my thinking on the matter, as I continue to go back and forth.

At one time or another in the last fifteen years, I’ve reviewed, if not every email client ever released for the Mac, at least a pretty good portion of them. Every client has some special advantages, and to be honest, I seem to have an urge for new user interfaces now and then that causes me to switch email clients somewhat promiscuously. At one time or another I’ve been a fan (and user) of Eudora, PowerMail, Outlook Express, Thunderbird, Mailsmith, Gyaz Mail, Sweet Mail, Apple’s Mail (a.k.a. “Mail.app”), and a couple that I’m probably forgetting.

But as it happens, I think I was one of the first people on the planet to get an invite to use Gmail, back before anybody had heard of it. I didn’t think much of it for a long time. But several years ago I decided that Gmail has two decisive advantages. First, it’s web based. That means I can get my email from any device or any computer that I have access to. If my main computer dies suddenly, I’m not locked out of my mail — I just switch to a different computer and log in. And second, as it turns out, Gmail happens to have just about the best user interface of any email client I’ve ever used. By “best”, I don’t mean “prettiest.” I mean the most usable, the one with the features I need most, implemented in a way that makes them easy to use. And so, for the last many years — I think it must be about four years or more — I’ve been using Gmail for all of my mail. For me, that’s a long time to use the same application!

But now, with the new and, in my opinion, much improved version of Mail in Lion, I’m reconsidering my options.

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Mail’s advantages

Here are the new Mail’s relative advantages, as I see them:

1) With Mail, I’m able to get all incoming messages to land in a single universal inbox. This completely eliminates the need to switch from one account to another. I use four different email accounts on a daily basis, for different purposes, and I need to stay on top of all four of them pretty closely. Working with Gmail, I have to keep switching from one tab to another in my web browser, and with some of the changes Gmail has made recently to the management of accounts, I actually have to switch accounts in the same tab. Mail eliminates that, which is a big plus.

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Gmail’s advantages

On the other hand, Gmail has some serious advantages, too.

1) Gmail integrates perfectly with its own additional services like my calendar, Google documents, etc. This integration is possible with Mail and iCal, too, but it’s not as easy. Addendum: If I used iCal and relied on the Mac Address Book more than I do, then Mail would win this point. But I don’t.

2) I am completely in agreement with Gmail’s no-folders approach. There is no point to putting things in folders whatsoever. What matters is that you can find stuff when you need it. And if Google can’t find it, it can’t be found; well, what I mean is, Google’s find feature is tops. Gmail does support labels, and labels are much more useful than folders, because you can attach multiple labels to the same message. I find the folder hierarchy in the drawer on the left in Mail rather confusing by comparison, especially since it combines all my accounts into a single view.

3) Gmail supports a large number of add-ons that have proved to be very useful. The most useful one is probably the ability to change my mind after I hit the send button — at least for a few seconds. This one has helped me out many times. Second, I like the fact that Gmail can (usually) recognize that I wrote something like “See the attached file” but in fact forgot to attach the file. A third utility I use only occasionally but really like when I need it is Baydin’s Boomerang, which lets me ask to be reminded about an email in N days.

I won’t mention Google’s alternate mailbox views, including Priority Mail view, because, although I’m intrigued by these options, I haven’t quite gotten used to them and generally I have stuck with the classic inbox, where the last message to arrive is shown at the top of the listing.

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Neither pro nor con

There are a couple features that could be considered a pro for one client over the other, but which aren’t so important to me.

First, there’s the ability to access my mail from any computer, which I mentioned near the start of this article. That isn’t really an advantage for Gmail over Apple Mail, because I’m using Apple Mail as an IMAP client to access my Gmail accounts. So my mail is still stored on Google’s servers — everything except drafts. If I were to decide to use Mail as my main client on my iMac, and (heaven forfend!) if my iMac were to die, I could still go to my iPad, or even open a Windows laptop and get to my email using Google’s browser UI. I will never use an old-fashioned POP mail account again, if I can help it. But this just isn’t an issue any more.

Second, there’s the fact that Mail downloads my messages to my computer and Gmail doesn’t. If I was paranoid about Google losing my mail, this would matter to me. I know some people really are concerned about this and I don’t say it’s not a valid concern. But my view is, Google is much likelier to keep my mail backed up than I am (although I do backup routinely). And having all that mail on my computer takes up a fair bit of disk space. So this is a wash.

Third, with a desktop mail client (whatever it might be), URLs in other applications that are designed to send email (“mailto” URLs) work properly, opening the desktop app (Mail, say) and creating a new message. If I was clicking a lot of mailto URLs in, say, word processing documents or PDFs that I’m reading in Preview or in FileMaker Pro, well, then it might matter. But as it happens, this just is not a problem for me more than, oh, once a month, if that often. And if this really mattered to me, I could eat my cake and have it too by using Mailplane, which turns Gmail into a desktop application that you can set as your default mail client.

Finally, there’s the esthetic factor. This, I think, is a wash, or nearly so. To my eyes, the new Mail is nicer to look at. There’s very little “eye candy,” rather, it’s just got a nice clean UI. It’s easy on the eyes in the more or less literal sense, and that’s important, given how much time I spend every day doing email. Gmail has recently updated its user interface, too, and the new UI is certainly less cluttered than the one before it. So while Gmail still isn’t quite as pretty on my iMac as Mail is, it’s pretty enough. By the way, the mobile UI for Gmail that I see when I access Gmail in Safari on my iPad is nicer than the UI on my iMac. I wish they were the same, because I rather like the UI on the iPad. It’s very similar to the UI of Mail.

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Mailplane

Speaking of Mailplane, I’ve given it a serious trial. Mailplane is basically a web browser that is dedicated simply to displaying your Gmail accounts. That means you get all of the advantages of Gmail, but you get them in an independent application. Mailplane has a number of other features not found in Gmail (for example, drag and drop attachments, ability to take screenshots, support for Growl notifications) that someone else might think are terrific but that I myself don’t find compelling.

There seem to be three opinions about Mailplane. A number of people I respect (folks who write for Tidbits) think it’s great. A second group of people think Mailplane is nice, but a bit pricey. And then there are those who don’t quite see the point. I’m afraid I’m in the third category. It certainly is very nice, I guess, and if I saw the point, I wouldn’t think $25 was too much to pay. But I just don’t find it that difficult to manage a couple tabs in Safari or Chrome for my different email accounts; and Mailplane does not give me a universal inbox, as Mail does. When I want to switch from my Polytrope personal account to my Polytrope support account (or my personal @gmail.com account, or my photography practice account), I have to double-click that account in the accounts drawer and let the new account load. This is slower than clicking on a different tab in my browser. Used to be that Google wouldn’t let you have more than one Gmail account open at a time. That’s kind of still true, but now there’s a fairly easy “switch accounts” UI in Gmail that I find as easy and quick to use as switching accounts in Mailplane.

Mailplane shares one advantage with mail: you can configure it to handle mailto URLs. But as I said above, that’s just not a big deal for me.

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So?

Well, now that I put it down in writing, it’s looking like, as much as I’m tempted by that universal inbox in Mail, I’m going to have to stick with Gmail. On the other hand, I’m very fickle, so a week from now, who knows, I could have switched to Sparrow (which is actually quite nice, sort of Mail Lite).

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Addendum a day later…

Well, I thought this decision was going to be easy, after I’d cleared my head on the matter by writing this article. Wrong. Turns out that Apple Mail’s one advantage — the universal inbox — is a really compelling advantage. So I’m still going back and forth!