I must give clear warning from the gates, I'm a longtime Google and Gmail fanatic. But great as it is, even Gmail is not a "one size fits all" solution. In fact, many of the folks I speak to dislike Gmail!
Incomprehensible as I find that, it's a fact. But those folks still want a modern email solution. They just want something that is closer to their comfort zone. Outlook, or some other email client software, is frequently at the center of that "warm and fuzzy" they hate to abandon.
As a computer pro, if I'm going to give an opinion I need to base it on actual experience, not fanboi prejudice. Outlook.com has all the earmarks of a legitimate contender. So... the Gmail acolyte abandoned Gmail, for a month. Here's what I learned:
Gmail Pro's/Cons:
GOOD:
Gmail organizes your email into "conversations", or "threads". If you have ever read the comments or discussion after almost any web news article, Gmail conversations will look perfectly normal and accessible to you. As messages come and go, they get grouped according to the subject line of the original email, no matter how long ago the "conversation" started. When someone replies to you, that reply is added to the bottom of the conversation, with all other correspondence in that thread collapsed above it. You can easily open up the preceding messages, and see who said what, and when, in neat and logical order, with no pawing thru folders to find messages from weeks or months ago. This is gold if you need to be able to review and track who said what. You can send a mass mail to hundreds of people, and when anyone replies to that email, it's automatically added to that conversation. Project Managers, Geeks, busy Exec's, Professionals of all stripes... If you live and work in your email, and for some reason you have never tried Gmail, trust me on this one!!! Conversations are exactly what you want to see.
GOOD:
Gmail (of course) seamlessly integrates into the whole Googleverse, particularly if you use an Android Phone. Google+, Drive, Docs, Maps, Picassa, Voice, Youtube, etc, etc... I could go on for an entire book on this one subject. Many books HAVE been written on this subject! But no one needs to read them, we just use all the tools and toys Google provides, easily and intuitively, never opening a help file. Suffice it to say MS has it's work cut out for it to try to match this.
GOOD:
Gmail Search. Second to none. This is as you would expect from a mega-corporation built on the world's best search engine. From the very beginning of Gmail, this one feature was intended to make folders, rules, filters, flags and various other sorting and filing mechanisms completely obsolete. And if you embrace it, you will find that it succeeded. Gmail has since added labels and stars and flags and circles and a half dozen other methods of sorting, filing and organizing for the compulsive types who simply must. But the simple fact is you don't need them. Just archive 90% of emails and delete the trash, as they come in. Then search if you need to refer to something. I can find an email from 2007 every bit as fast as something I got last week. And FAR faster than anyone who has to look thru folders they created!!! Searching your email just plain works, and works damn well.
And there's another imponderable benefit. All that time that you formerly used creating a folder system, sorting and filing email, and pawing thru folders when you need to find something... you can now use to get some actual work done. Or play more Candy Crush.
BAD:
A significant percentage of people find ALL of Google's offerings counter-intuitive. From Chrome to Gmail to Drive and Maps to Picassa and on and on... Strangely, Google has simplified and cleaned and pruned and streamlined and changed the paradigm so much that some folks find all Google offerings frustrating and baffling. Particularly those who are accustomed to Microsoft ways of doing things. They try something Google, "can't find anything", and soon revert. I remember I felt this way a few times, back when I first tried Google products. And it's worth noting that not everyone is willing or able to make the change, no matter how many times family and friends enthuse about how wonderful it all is.
And the ones who are complaining aren't wrong! Despite Google's justly deserved fame for designing simple, user-friendly, intuitive interfaces, those same interfaces are a problem to many thousands. Especially to those who have learned to use Microsoft products by rote, with no real understanding... Google products can be a nightmare.
Outlook.com Pros/Cons:
GOOD:
Sweep feature/filter creation. The Sweep feature in Outlook.com is superbly conceived and executed. It's essentially the same as making a new rule in Gmail or even the old Outlook, but far simpler and less intimidating for non-geeks. I remember when the old Outlook filters and rules were BAD. Horrifically complex, and intimidating/frightening for non-techies. This approach is very good indeed. You select an email, click Sweep", answer very simple questions, and voila, you created a rule/filter.
BAD:
The conversation feature is considerably less than stellar on Outlook.com. Yes, there is an available setting to organize messages by conversation, but it just doesn't work as well. In fact, I found it quite frustrating compared to Gmail's elegant simplicity.
GOOD:
FOLDERS! I know, it's strange. I've already addressed that with Gmail, you don't need folders. Nope, not at all. But for whatever reason, a great many people like Outlook style Folders better than Gmail Labels. Even though it's clear to anyone who looks at it dispassionately that Gmail's Labels have more utility, and better functionality. And notwithstanding that Gmail's search makes all organization and folderization superfluous, see above... Folders just SEEM easier! Homey. Comfy as faded old patched jeans. I'm pretty sure this goes back to the roots, when we all learned to use Windows.
GOOD:
Cleaner interface. Many folks have belaboured this, so I won't, I'll just add my vote. Yes, Gmail themes are prettier by far, and Gmail is more customizable, in every aspect. But Outlook.com appears simpler, cleaner, more attractive. Cleaner wins.
BAD:
I desperately miss Gmail's Send and Archive feature!!! It's annoying to see an email I just answered still sitting in my inbox. I answered the damn thing, I should be done with it! But I still need to stick it in a folder, or create a new folder, or archive it, or something. After Gmail, being forced to make time wasting decisions in order to maintain a clean inbox is offensive. Outlook.com should at least allow me to Archive it automatically when I click Send. I looked for this, didn't find it.
GOOD:
It's Outlook! Even after "X" years of Gmail, coming back to Outlook feels like coming home to Mom's chocolate chip cookies. How it manages to be so shiny and new and streamlined, and yet it's undeniably the same cozy old Outlook... it's beyond me, but very impressive indeed. So yeah, going home is nice. I seem to remember I moved out for a reason... but damn those cookies are tasty!
GOOD:
The Outlook.com apps I tested (Android, iPhone, and iPad) were all quick, clean, and dovetailed nicely with each other. Full marks to Microsoft for making this a truly device independent solution.
GOOD:
Outlook.com integration with other MS services is far and away better than I expected. Calendar, Skydrive, Bing Maps, dead easy messaging and social tie ins... Microsoft has done a staggering amount of work to make it all flawless and non-intimidating. Some might say they copied Google for some things, even several things. But that's rampant in this industry, and who cares, ultimately, if it works? The upshot is Microsoft is able to beat Google in some important ways here, particularly for the non-technical. The MS offerings largely just plain work, often with zero install or config. At least that's the case on a PC, which should come as no surprise. It's simple home court advantage. Google has the same "zero config, it just works" advantage on Chrome OS, or an Android phone. I still have to give Google the win on this one for more and better free tools and toys, but it wasn't near the blowout I anticipated.
GOOD:
Outlook.com email search is excellent, and lightning fast. Miles better than older "client" versions of Outlook. Without making scientific or laborious comparisons, it feels a bit different, but quite competitive with Gmail. This one point alone makes all my misgivings pale into insignificance. Outlook.com may not be perfect from a Gmail acolyte's point of view, but excellent search at least makes it livable.
Conclusions:
The day of email client software is long gone. Email clients were created back in the bad old 56k modem days, primarily to make the glacial sending or retrieving your email into something automated, something that could happen while you went for coffee. With today's advances they are as obsolete as 8-tracks. They greatly increase the likelihood of losing all your mail and contacts someday, and they usually tie you to a single machine. Despite many improvements in syncing and communication between devices, as well as a plethora of backup solutions, web-based email is still inherently simpler and safer. Hence the rise of Webmail: Yahoo, Hotmail, Gmail, et al.
Gmail has been the King of Webmail for quite some time now. I expected Outlook.com to be lame and pokey in comparison, as outgunned as Moped racing a Ferrari. To my surprise, I found valid (and sufficient, for many) reasons to switch from Gmail to Outlook.com. For lots of folks, the Outlook comfort factor and clean design trumps Gmail's superior tech and more efficient paradigm.
For myself, I will be returning to Gmail. But not without respect for what Microsoft has done. The contest was miles closer than I anticipated. If you are one of the many who have resisted for years, and in particular, if you still use Outlook or Thunderbird or some other client, then you probably know you need to make a change. Outlook.com may be your perfect and long awaited answer. Outlook.com is a completely modern webmail, accessible from almost anything, anywhere. And the bonus is you get to stay in your comfort zone! In fact, it may be more comfortable than any other version of Outlook, ever.
If nothing else, Gmail finally has a worthy competitor.