Microsoft recently announced its latest attempt to be a playa in the Internet, called Windows Live Mesh. As former Microsoftie Joel Spolsky opined, Live Mesh is not the first time Microsoft has tried a master plan for connecting everything via the Internet. It's not clear how this effort will end any better for Microsoft than the last one.The first attempt that Microsoft made at everything-to-everything connectivity was about eight years ago, and was code-named HailStorm. Microsoft's master plan didn't go quite the way they hoped, and HailStorm was never released. One of the remnants of that effort is Passport, now renamed and known as Windows Live ID. But in the meantime, people have figured out how to craft their own connectivity using everything from RSS feeds to Twitter.

PC history is about the rise and fall of one-trick ponies. Ashton-Tate had dBase, Lotus had 1-2-3, Satellite Software (later WordPerfect Corp.) had WordPerfect, Novell had NetWare, and Software Publishing had Harvard Graphics. Each one of them was a Goliath at some point, and fell to earth with a thud as they were unable to adapt to changes in the PC market. Not coincidentally, nearly all of them were brought down by Microsoft. Now the tables are turned.

Although Microsoft itself is more like a two-trick pony (Windows and Office), those two product lines still bring home nearly all of Microsoft's bacon. They also bias Microsoft's perspective on new ventures. For example, could Microsoft build its own competitor to Google Docs? Sure they could -- but why would they undercut the Office cash cow? And now that they are far behind in the Internet space, they hope a grand and expensive plan can vault them to the front.

So, Microsoft bolsters a lagging Internet effort by making an offer for Yahoo and announcing Live Mesh. It's a flashback to the death-spiral efforts of Borland buying Ashton-Tate and Novell buying WordPerfect. The difference, of course, is that Microsoft has a lot more money and can recover from mistakes. HailStorm may not have stuck to the wall, they may think, but Live Mesh has staying power.

I have concerns about the complexity of the Live Mesh plan, at least as far as it's been revealed. Ray Ozzie is a smart guy, no doubt; he's best known as the original architect of Lotus Notes. But if you ever used Lotus Notes you know that there's a big difference between a great idea and a usable product. As I suffered through using Notes in a former job, the IT department told me that it was a really great foundation for developing business apps but they just needed to spend more time developing them on the "Notes platform." Is that going to be the story of Live Mesh as well -- a bunch of quality parts that can't easily be assembled into usable tools?

Between Microsoft's inevitable protection of its cash cows and the inherent complexity of this boil-the-ocean project, I don't think Live Mesh has much of a chance to deliver on its hype. No doubt, a few useful components will be built out and find a home inside Microsoft, the same way that HailStorm's Passport became Windows Live ID. But this grand plan is a bit too grand for me, no matter how exciting Robert Scoble says it is.