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Managing Your Life in the Clouds: A Guide for Windows Users, Part 4: Putting It All Together

Part 4: Putting It All Together

I originally approached this guide with the intention of providing some sort of advice about which company--Microsoft, Google, Yahoo, or Apple--offered the "best" cloud computing email and PIM experience. But it didn't take long for me to realize this would be a mistake. First, these products and services are evolving all the time, and as Apple's recent introduction of MobileMe shows, there's no reason to believe there won't be incredible, revolutionary upgrades every once in a while either. Second, everyone's needs are different. While I may find a particular service worthwhile across the board, you may not. Third, there's no reason you can't mix and match, using the best products and services from any variety of companies, including some we haven't discussed at all.

With that in mind, I'd like to begin wrapping this up with some general feature comparisons between each discussed cloud computing experience. I'll also explain which services I'm using right now and why. In the next and final part of this service, I'll look at ways you can overcome some of the current limitations.

The mile-high view: Comparing the services

By breaking down the previous comparisons (and my separate MobileMe review) into table form, organized by service--email, contacts, calendar, photos, and storage--we can see some interesting trends. For example, only Apple's MobileMe service requires to you pay a yearly fee, and my guess is that most consumers could get away with the free offerings from Microsoft, Google, or Yahoo! quite easily. On the other hand, the value of Apple's offering could justify the yearly fee, assuming the company ever gets it working correctly. I'm placing my bets elsewhere.

From what I can see, Microsoft's offerings are the most comprehensive and cohesive. No, Windows Mobile hasn't generated the same level of excitement as has the iPhone (heck, even the Blackberry has somehow managed to wrestle mindshare from Microsoft's mobile platform). But Microsoft offers a set of solutions that work across all of the necessary platforms: The PC, the Web, and mobile. If you're looking for a fairly seamlessly plug and play type experience, it's not a bad way to go.

Google seems to be the most spastic, but they're also moving the quickest, and the advent of the Android phone platform late this year could really redraw the map. I think Google's Web-based email and PIM offerings are superior to those from the other companies but, again, your mileage may vary.

I know there are those who love Yahoo! dearly, but aside from Flickr and their native mobile applications, I don't see a lot to recommend there. Couple that with the company's recent problems and a general haziness about Yahoo!'s future, and my gut feeling is that maybe Yahoo! should be avoided.

In any event, here's how the feature tables break down. I've marked a few items as red to denote problems I see as particularly serious. Please do drop me a note if you see any mistakes or omissions; it was sort of torturous making these tables and I'm sure I've left something important out.


A few notes about email services.

  • Storage doesn't matter anymore. I do list some storage limits here, but let's be serious: Storage is no longer a factor when choosing a Web-based email service. All of the services listed, with the exception of Apple, offer virtually unlimited storage and/or have publicly stated that they would simply raise limits as required by their customers.
  • IMAP is the baseline for email interoperability. That said, Microsoft's intra-ecosystem compatibility is close enough for those who go that route. If you are using a Hotmail-based email account, however, know that interop outside of Microsoft's products will be difficult.
  • Don't be fooled by native mobile support. Yeah, I list it, but as long as the service provides IMAP support, your mobile experience will probably be excellent.
  • Custom domain names are the wave of the future. Sure, my Gmail account works fine, but a account, running on Gmail, would be better. It would also be free (aside from the yearly domain costs). That's cool.
  Microsoft Google Yahoo! Apple
Web service Windows Live Hotmail Gmail Yahoo! Mail MobileMe Mail
Free version Yes Yes Yes No
Storage: Free version 5 GB Over 5 GB Unlimited n/a
Paid version $20 per year Additional storage $20-$500 per year $20 per year $99 per year
Storage: Paid version 10 GB 10 - 400 GB Unlimited 2 - 20 GB
IMAP access No Yes No Yes
Other client access Outlook 2003/2007 and Windows Live Mail POP3 POP3, but only with paid account POP3
Native mobile support Windows Mobile, Blackberry, Nokia iPhone, Blackberry, various Java-enabled devices iPhone, Blackberry, native mobile app on multiple devices iPhone
Mobile Web version Yes Yes Yes Yes
Domain names,, ( in certain worldwide markets),,,
Supports custom domain names Yes Yes No No


  • Sync is still a problem. Contact sync remains curiously problematic if you move outside of the Microsoft ecosystem. Google doesn't offer it at all, which is unreal. Yahoo! uses a crazy third party utility that was probably written in Visual Basic by a kid in his parent's basement. MobileMe offers great contacts sync, but the price ($99 a year) is extravagant. Many will be forced to manually import and export contacts and maintain multiple databases. That said, getting contacts synced to a mobile device is generally doable.
  Microsoft Google Yahoo! Apple
Web service Windows Live Contacts Gmail Yahoo! Mail MobileMe Mail
Free version Yes Yes Yes No
Native client sync Outlook 2003/2007 and Windows Live Mail No Microsoft Outlook, Outlook Express (XP) Microsoft Outlook, Outlook Express (XP), Windows Contacts (Vista)
Export to desktop CSV Google CSV, Outlook CSV, vCard Outlook, Thunderbird, Yahoo! CSV, vCard, VCF No
Import from desktop Outlook, Outlook Express (XP), Windows Contacts (Vista), Hotmail, Yahoo! Mail, Gmail CSV Multiple, via online TrueSwitch utility vCard (individual contacts only)
Native mobile support Windows Mobile iPhone iPhone, Blackberry, native mobile app on multiple devices iPhone
Mobile Web version Yes Yes Yes Yes


  • You pretty much need Outlook on the PC. If you have any desire to sync a Web-based calendar with the PC, you're pretty much going to need Outlook, which is silly for a number of reasons. First, free, industry-standards-compliant calendar applications, like Windows Calendar (part of Vista) and Mozilla Sunbird are readily available. Second, Outlook is expensive, and it doesn't even come with the most popular version of Microsoft Office any more.
  • If you can skip the desktop, do so. That said, who needs a desktop application? Any of the surveyed services offer a decent Web calendar, and all of them can be viewed on mobile devices of various kinds. (They all offer mobile Web versions as well.) If you don't have Outlook, but what you want is your calendar everywhere, access it from the Web on the PC and from your mobile device using a native application. And cross your fingers about native PC interop.
  • iCal is the future. The standard, not the OS X application. All modern calendars should fully support iCal publish and subscribe. Avoid those that do not.
  Microsoft Google Yahoo! Apple
Web service Windows Live Calendar Beta Google Calendar Yahoo! Calendar MobileMe Calendar
Free version Yes Yes Yes No
Desktop sync Microsoft Outlook Microsoft Outlook Microsoft Outlook, Palm Desktop Microsoft Outlook
Support iCal Publish Yes Yes No No
Support iCal Subscribe Yes Yes No No
Native mobile support No (per this post) Windows Mobile (via desktop sync), iPhone (via desktop sync) Mobile app on multiple devices iPhone
Mobile Web version Yes Yes Yes Yes


  • Viva la difference. All of these solutions are surprisingly different, so it pays to experiment. Upload some photos to each. See what you can do with them with regards to sharing, backing up, viewing, editing, and the like. You might be surprised to discover that you're a die-hard Google guy but love Windows Live Spaces for some reason. You never know.
  • Use more than one service. And pay for them. These are your photos, after all: Maybe you should consider uploading them to at least two different services. If you're looking at full-resolution backup, I recommend Flickr and Google Picasa Web Albums, though you'll actually want to pay extra for both, for additional storage and/or upload improvements.
  • Look into desktop integration. Pick a photo service that works with a local photo editing application like Windows Live Photo Gallery or Picasa. Sure, we may all be editing in the cloud some day, but for now it makes more sense to edit offline and then backup the results online.
  • But wait, there's more. Some of the best photo management services online aren't even discussed here. I'd pay particular attention to what Adobe is doing now with Photoshop Express. They seem to know a thing or two about digital images.
  Microsoft Google Yahoo! Apple
Web service Windows Live Spaces Picasa Web Albums Flickr MobileMe Gallery
Free version Yes Yes Yes No
Storage: Free version Unlimited, but uploads are limited to 500 photos per month 2 GB Unlimited, but uploads are limited to 100 MB per month n/a
Paid version No Additional storage $20-$500 per year $20 per year $99 per year
Storage: Paid version n/a 10 - 400 GB Unlimited 20 GB
Client integration Windows Live Photo Gallery Picasa Windows Live Photo Gallery, Flickr Uploadr, many others No
Mobile integration Windows Mobile No Multiple devices iPhone
Mobile Web version Yes Yes (with highly optimized versions for iPhone, Windows Mobile, Nokia S60 3g) Yes Yes


  • Look elsewhere for backup. While Microsoft's 5 GB limit on SkyDrive is fine for document storage, you're going to need to look elsewhere for backup-quality storage. And for that, you're going to have to examine solutions that fall beyond the scope of this overview. Here are two to consider: Amazon S3, which I use myself through the excellent JungleDisk utility; and Mozy. Both solutions are cost effective and worth investigating.
  • Pay for it. Free online storage is cute, but if you're backing up your crucial documents, photos, and other data, you're going to be paying for more storage. It should cost less than $10 a month and should be from a company you trust. Again, I use S3/JungleDisk.
  • Seamless experiences will aggregate storage across all offerings. Microsoft is surely working on this, but right now they have no notion of "Windows Live Storage" that is available across all of their services. Google sort of has it for Gmail and Picasa Web Albums only. Yahoo! has no clue. But Apple is mostly doing the right thing, though they lack a free version. Here's how it should work: You get a bit for free, and pay a yearly fee for more. The more you use, the more you pay. Simple, right?
  Microsoft Google Yahoo! Apple
Web service Windows Live SkyDrive No Yahoo! Briefcase MobileMe iDisk
Free version Yes No Yes No
Storage: Free version 5 GB n/a 30 MB n/a
Paid version No No (can buy additional storage for Gmail and Picasa Web Albums only) No $99 per year
Storage: Paid version n/a n/a n/a 20 GB

What I do

OK, I'm sure you can scan tables of data as well as the next guy. The big question here, of course, is what do you do about it? With the understanding that everyone is different and has different needs, here's what I'm doing.

PC client. I use Windows Vista, of course.

Mobile. My smart phone is an Apple iPhone. I feel this offers tremendous advantages over other mobile offerings, but I recognize that Windows interoperability isn't where it should be, because Apple treats Windows users like second class citizens.

Email. I use Google's Gmail service for email, and have been using it full-time since early 2007. Gmail offers a tremendous Web interface if what you're looking for is speed and efficiency, as I am. Its spam filtering is excellent, which is crucial. I do not use a dedicated email client on the desktop because I use so many different PCs and moving Outlook data from PC to PC is a disastrous and error-prone activity. Gmail works well on the Web, works fine on the mobile Web, and integrates nicely with the iPhone's native email application thanks to its support of the IMAP standard. Consider the job done.

Contacts. To say that I have thoroughly mismanaged my contacts database to date is an understatement. In my defense, Google's Gmail-based contacts functionality was until very recently completely unusable. They've fixed this, so one of my goals this month is to consolidate and update my contacts there. Right now, however, I have separate contacts lists in Windows Live Contacts and Yahoo! Mail. I know, I know.

Calendar. I use Google Calendar for my scheduling needs. One limitation I've learned to live with is that, while Google "supports" multiple calendars (with color coding, etc.) you can't actually share anything other than the first, primary calendar. So that's all I use. I sync Google Calendar unidirectionally to Outlook with Google's free Google Calendar Sync utility so that I can sync my calendar to the iPhone.

Photos. I use Google Picasa Web Albums to store full-resolution backup copies of all of my photos. I'm currently paying for 40 GB of storage (and using about 30 GB of it). This costs $75 per year. I also backup my complete photo collection to Amazon S3 via the JungleDisk add-on for Windows Home Server. This costs about $5 a month. I have some favorite photos on other services as well, such as Flickr, MobileMe, and Adobe Photoshop Express, mostly for testing. I do pay for a Flickr Pro account as well, though I use that mostly for work-related photos.

Storage. As noted above, I backup photos to Picasa Web Albums and S3. I use Windows Live SkyDrive and Office Live Workspace for online document storage. I also backup data from my Windows Home Server to USB-based backup drives, which are stored offsite.

Next: Overcoming limitations...

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