Can You Spare 60 Minutes for Microsoft?

Microsoft (MSFT) is set to discuss its Windows strategy for enterprise customers on Sept. 30 in San Francisco. I'm intrigued -- Will Windows 9 fix the Windows 8 debacle? -- but confused on multiple fronts.

Consider this:

  • Apparently, the big Microsoft event is only one hour, and only about 50 people are attending, according to the Windows Weekly podcast.
  • Most hotel rooms in San Francisco are already booked solid at inflated nightly rates. Why? Because the massive Oracle OpenWorld 2014 conference -- which attracts roughly 60,000 people -- is in town.
  • Google will host an online conference -- Atmosphere Live -- one day after Microsoft's face to face conference.

So let's look at Microsoft's event invite in my real-world language:

"Dear Journalist, please come to San Francisco for one hour to hear about our Windows in the enterprise strategy. For those flying in to attend, please navigate around Oracle OpenWorld 2014 and open your wallets extra wide because any remaining hotel rooms cost a fortune. Once our event is over, watch Google's rival enterprise event online from the comfort of your laptop, tablet or smartphone."

I give Microsoft watchers like Mary Jo Foley and Paul Thurrott huge credit. Both hard-charging journalists are flying across the country to attend the 60-minute gathering in San Francisco. If I was still covering Microsoft as part of my media beat, I'm sure I'd do the same.

I like a lot of Microsoft's recent moves -- especially in the cloud. If the Azure cloud had its own tracking stock, I'd be buying shares regularly. But Microsoft also continues to confound me on some fronts. Scheduling a brief, face-to-face gathering in San Francisco the week of Oracle OpenWorld 2014? Instead of clicking Start... why didn't someone say "stop?"