For years, I’ve used and recommended Microsoft’s Live Mesh service as the ideal way for Windows users to sync folders between PCs and the cloud. But with Microsoft deeply integrating SkyDrive into Windows 8, Windows Phone, and, eventually, the Xbox, I’ve begun transitioning from Live Mesh to SkyDrive. Here’s what you gain—and what you lose—by doing so, and some tips for making the transition.

Live Mesh and SkyDrive: How we got here

The path that Microsoft took to its current vision for consumer-oriented cloud computing services is almost too convoluted to describe. The short version is that under Ray Ozzie’s unsteady hand (2005-2010), Microsoft offered a bizarre collection of ever-changing and often competing services that included (but probably isn’t limited to) Live Mesh, Windows Live FolderShare, SyncToy, and Windows Live Sync. But emerging on the other side of this nonsense, Microsoft finally decided that Windows Live Sync was the winner and would continue forward. So it promptly killed off the other tools … and then renamed Live Sync to Windows Live Mesh just to make things even more confusing.

OK, whatever. For the duration of Windows 7’s active lifetime (2009-2012), Microsoft pushed Windows Live Mesh through its free Windows Live Essentials suite, a set of applications and services that “completed” the Windows 7 experience (in Microsoft’s words); Essentials includes applications like Windows Live Mail, Messenger, Photo Gallery, and Movie Maker, all of which are excellent.

Live Mesh is a PC-to-PC-to-cloud folder sync service, like Dropbox on steroids. It lets you sync an unlimited amount of data between PCs using an arbitrary number of synced folders, each of which can exist in different locations on the hard drive of each synced PC. It also let you sync 5 GB of that data to the cloud, and provided a few other unique and useful services, including remote PC access (essentially Remote Desktop Connection over the Internet) and PC-to-PC settings sync for Internet Explorer and Microsoft Office only.

On the cloud side, Microsoft also offered its Windows Live SkyDrive service, which has recently been rebranded simply as Microsoft SkyDrive, since the Windows Live brand is being discontinued. Until recently, all SkyDrive users—which is to say, “anyone with a Windows Live ID,” or what will soon be known as a Microsoft account—received 25 GB of free, cloud-based storage. But since Microsoft didn’t offer any way to connect that storage to Windows 7 through Windows Explorer, that 25 GB of space was effectively useless and went largely unused by most. (Yes, you could use third party tools like SDExplorer to connect SkyDrive to Windows Explorer, providing drag-and-drop access to that cloud storage, but most people didn’t know such things were even possible.) Those that did use SkyDrive generally put up with the web-based interface, which offered limited uploading capabilities. And SkyDrive only “natively” supported Office documents and other common document formats and photographs. (Still does, actually, though that will be changing this year, I’m told.)

The relationship between Windows Live Mesh (which I’ll just call Live Mesh from here on out) and SkyDrive has been complicated, however, and confusing. In addition to the 25 GB of largely unusable SkyDrive-based cloud storage, Windows 7 users who installed Live Mesh as part of Essentials gained access to that service’s 5 GB of synced, SkyDrive-based cloud storage. But that 5 GB doesn’t come out of the 25 GB you get with SkyDrive; it’s additional. It’s also completely separate, and there’s no way to copy or move files between the two storage pools in the sky. Furthermore, while you can view documents and photos stored in SkyDrive through skydrive.com, you can’t do so with your synced Live Mesh folders. These things look and work completely differently and aren’t connected in any way.

I used Live Mesh quite extensively over the past three years, syncing various folders between my PCs and making it a central part of my workflow. However, until recently, I barely used SkyDrive at all, treating it (as most users did, I bet) as more of a curiosity than an actually useful service.

And then everything changed. Actually, it’s still changing.

2012: SkyDrive comes into its own

For the past several months, Microsoft has been slowly revealing its plans for the future, for Windows 8, of course, but also for related products and services that include such things as Windows Phone, Office 2013, the Xbox, and more. And part of those plans includes a sudden, deep reliance on SkyDrive as the centralized, cloud-based storage that will sit behind its other initiatives. We had seen a glimpse of this future in Windows Phone, which provided some SkyDrive integration even in its first, 2010-era edition.

But this year it’s all coming together.

First, and in a major strategy shift, SkyDrive is no longer cut off from the rest of the Microsoft ecosystem. The company has released a SkyDrive app for Windows Phone and SkyDrive applications for Windows Vista, 7, and 8, and has integrated SkyDrive in Windows 8 through a Metro-style SkyDrive app and cloud-based settings sync. SkyDrive apps are also available for the iPhone, iPad, and Mac, and Android versions are on the way. This means that it is, or soon will be, possible to seamlessly access files and folders in your SkyDrive storage from virtually any computing device on earth. (How Microsoft will integrate SkyDrive with the Xbox 360 console and Xbox services like Xbox Music and Video remains to be seen. But it’s coming.)

Second, and perhaps more important, the Windows-based SkyDrive applications provide the all-important PC-to-PC (and PC-to-PC-to-cloud) sync functionality that was previously offered through Live Mesh, albeit in a less configurable (and complex) way. That is, you can’t sync some arbitrary number of folders across your PCs; instead, you sync a single SkyDrive folder that maps to your storage on Skydrive.com. You can’t configure some folders within that folder hierarchy to sync only to certain PCs, and everything must sync to the cloud as well.

This sounds confining perhaps, but in this era of simpler devices, maybe it’s time to stop overthinking things and not worry about micromanaging our PC storage. And as I’ll describe in my own use of the SkyDrive app below, you can easily map parts of SkyDrive storage to your Windows libraries (Documents, Music, Videos, and so on) if needed, and you don’t need to resort of arcane files system hacks as some other misguided souls may suggest.

Third, Microsoft has proven it’s serious about SkyDrive by finally offering paid storage tiers. If you were using SkyDrive previous to the release of the SkyDrive beta application for Windows, you were grandfathered in with your 25 GB of free storage. But while new SkyDrive users “only” get 7 GB of storage for free, that’s still better than what the competition offers: Apple and Google provide just 5 GB of free storage on iCloud and Google Drive, respectively, while Dropbox offers just a paltry 2 GB.  And Microsoft’s paid storage offerings are better than the competition, too: You can grab an additional 20 GB for just $10 per year, 50 GB for $25 per year, and 100 GB for $50 per year. These prices nicely undercut the others by a wide margin. It’s not even close.

And finally, while SkyDrive does not offer the same remote desktop capabilities as does Live Mesh, it does offer a solution called Remote Fetch that I think actually answers the real need here, which is to remotely access files on your other PCs. So instead of RDPing into a remote PC, you can simply use the SkyDrive web interface to navigate through the file system of your other PC(s), and then copy files over as needed. Excellent.

(If you do really need Remote Desktop for some reason, I have a free solution for that, too. Simply install LogMeIn Hamachi, a VPN solution that is free for personal use on up to five PCs. I use this regularly and its proven invaluable when I’m on the road and need to actually interact with a computer or server at home.)

SkyDrive in beta: It’s not perfect (yet)

The SkyDrive application for Windows isn’t perfect. In addition to its inability to arbitrarily sync individual folders around your PC’s file system—which, again, I’d argue is perhaps a bit too complicated for most people anyway—there are two key things missing here that I hope (and expect) to see Microsoft address. (Since the SkyDrive application is still in beta, this is a reasonable assumption.) These include:

Choose which folders to sync. Currently, when you install SkyDrive on your PC, the service is either on or off. If it’s on, the entire SkyDrive folder structure is synced to the PC, so if you’ve actually used up that 25 GB of free space (or whatever), you’re going to sync 25 GB of stuff to the PC whether you want it all or not. This isn’t a huge deal on a PC with a 128 GB SSD drive, but on tomorrow’s Windows RT and 8 devices, which will start with just 32 GB and 64 GB of storage, that’s a deal breaker. And if you’ve opted in with extra storage, as I have, that SkyDrive stuff could eat up your PC storage quickly, no matter how big it is. The solution, of course, is an interface where you choose which folders within SkyDrive that you wish to sync on a PC-by-PC basis.

Shared folders. While SkyDrive does offer nice sharing capabilities from the web, the SkyDrive Windows application does not, and it does not bring across any shared folders. So if someone is sharing a SkyDrive folder with me, I won’t see it from the SkyDrive folder structure in Windows. The solution here, of course, is for Microsoft to provide this capability, combine it with the choose folder sync capability noted above (so some other person can’t overwhelm my storage by mistake), and then provide a way from within Windows to share SkyDrive-based folders with others.

How I’m using SkyDrive

I mentioned previously that I’ve been using Live Mesh for past three years or so, and that it’s been a key part of my workflow. With the changes to SkyDrive, however, I’ve been moving to Microsoft central cloud storage instead, and while it took a while to figure out how I’d transition, I’m now effectively all-in. There is one sticking point, however.

I’ve been using Live Mesh (and before that, it’s predecessors) to sync the folders for my books between PCs and the cloud, using this replication capability as an implicit “offsite” backup of sorts. I assume it’s obvious why that’s valuable, but it’s probably not hard to imagine that moving the book folders from Live Mesh to SkyDrive would achieve the same result. What’s missing, however, is the sharing (as noted above). Two of my three most recent books, Windows 7 Secrets and Windows 8 Secrets, were collaborative projects and my co-author, Rafael Rivera, and I share the folders for those books through Live Mesh. So as either of us adds or edits content within those folder structures, the changes are replicated instantly on the other’s PCs.

SkyDrive doesn’t offer this capability, at least not yet. So as of today, the only folder I have remaining in Live Mesh is for Windows 8 Secrets (and we’re wrapping the writing up this month as the product barrels towards RTM). I’ve moved everything else to SkyDrive. And, as important, I’m starting to rearrange my SkyDrive storage in a way that is simple and efficient.

First, the Live Mesh stuff. Before moving to SkyDrive, I synced several folders through Live Mesh. Aside from the book folder(s), these included:

Docs. This small folder contains very few files, and so it syncs very quickly, but some of them are very valuable, such as my software product keys, Penton information, and so on. I would sync this folder to my Documents library.

eBooks. A collection of PDF- (and ePub- and mobi-) based eBooks and related documents. I would sync this folder to my Documents library.

Favorites. This contains favorite photos of family, friends, and places we’ve visited. I would sync this folder to my Pictures library.

Work. My “work” folder for ongoing full-length articles (like this one) and article series (“Windows 8 Tips,” “Windows 8 Feature Focus,” and so on). This folder is pretty large, and of course includes all of the screenshots and promo graphics that accompany those articles, in addition to the documents themselves. I would sync this folder to my Documents library.

Copying these folders into the SkyDrive folder structure was of course straightforward, as was then removing them from Live Mesh. (I then temporarily archived the originals on a few PCs before deleting them after being sure it all worked normally.) And by just doing this, I removed one set of configuration steps I’d have to undergo with each new PC install, where I’d install Live Essenitals, and thus Live Mesh, and then need to manually point each folder share to the right location on disk. With SkyDrive, you just install the application and it all syncs.

But I wanted to make SkyDrive even more efficient for daily use on my PCs. There are two ways you can do this, I guess. You could simply configure the folder structure within SkyDrive the way you want, a one-time configuration that will replicate to the cloud and across each synced PC instantly. Or you could do a bit of Live Mesh-style folder configuration with each install, and reorient your Windows libraries so that they use the appropriate locations in SkyDrive, rather than their defaults.

The first of these approaches is obviously valuable on a fairly universal basis. The second is available for those who simply can’t let go of micro-managing their computers. I’m trying, but I understand it’s hard.

How you configure SkyDrive’s folder structure is (mostly) up to you. While some folders (like SkyDrive camera roll, added by Windows Phone if you set up cloud sync of pictures) can’t really be moved (they’ll simply return if you try), most can, and you’re free to set up whatever structure you wish. For example, you could replicate the libraries scheme from Windows and have top level Documents, Music, and Pictures folders, if that makes sense to you.

I currently have a slightly more convoluted SkyDrive folder structure since I’ve been using the service for a while and I’m still in the process of moving things around. Some folders, like the one that contains the OneNote-based show notes for Windows Weekly, I’ll likely just leave as-is. But what I’m looking at, I hope, is something that will one day be as simple as this:

skydrive

Inside those folders, of course, you’ll find some familiar faces from Live Mesh. I placed the Docs, eBooks, and Work folders under SkyDrive/Documents, and Favorites is under SkyDrive/Pictures. It’s simple, and it works well.

You can also take it a step or two further.

If you have applications you use frequently, you might configure them to use a SkyDrive-based save folder, for example. In Microsoft Word 2010, you configure this in File, Options, Save, and as you can see here, I’ve configured the Default file location for a SkyDrive-based folder:

word-save

Or, you could re-configure your libraries. This step is more involved, but if you’re not re-installing Windows a lot as I am, it may make sense to do this.

For example, let’s see how we might configure the Documents library to use SkyDrive by default instead of the normal location(s).

Navigating to Documents in File Explorer, tap Manage and then Manage Library in the ribbon to display the Documents Library Locations window. By default, there are two folder locations configured here: Your My Documents folder is listed as the default save location and the Public Documents folder is listed as the public save location.

library-01

Now, I don’t know about you, but I never use the Public library folders, so my first step is to remove that from the library. (This makes the My Documents folder the default save and default public save location). Then, you can tap Add to add a new location. I chose the Documents folder in SkyDrive (C:\Users\Paul\SkyDrive\Documents in my case).

library-02

Now, you can configure this location to be the default for saves. Right-click the SkyDrive Documents entry and, in turn, choose each of the three following options from the context menu: Set as default save location, Set as public save location, and Move up.

library-03

(I choose to leave the old Documents folder in there as a secondary folder for a variety of reasons: I still use it for Live Mesh, but more important, some apps simply write to this location regardless of the changes you make here.)

When you’re done, the library will utilize SkyDrive by default, and any documents you save or edit here will be replicated to the cloud and across your connected PCs. You can of course do the same for your other libraries, if needed (but remember that SkyDrive—for now—only understands Document and Picture file types in the cloud).

library-04

There are more complex things you can do here using symbolic links and other file system hoo-hickery. But I don’t see the value in that. Again, tech enthusiasts tend to overthink things, and even this mapping of libraries is borderline compulsive. But it does get the job done.

If you have any hints or tips for maximizing your use of SkyDrive in Windows, I’m all ears. Let me know what you think.