This is the second article on a real-life experience upgrading from Windows Vista to Windows 7 (the first is available here).

The first Windows Vista to Windows 7 upgrade I successfully completed was pretty straightforward because the starting point was a clean PC.  Not very many applications installed.

This second example was a different story because I decided to upgrade my primary work PC (a notebook with multiple years of applications installed and configurations set).  The no surprises approach to changing operating systems is to completely back-up your work, install the new operating system from scratch and then restore all data and applications.  Painful - too painful (the equivalent of buying a new house, packing up all your stuff - moving - and setting up again).  And Windows 7 brings with it the promise of a true upgrade path.

With support.com IT's blessing I went for it - over a weekend - with the possibility I'd be offline and scrambling on Monday if something went wrong.  Here is the story:

I chose to go with Windows 7 Ultimate (there are multiple editions from Starter to Ultimate).  I logged into my PC, popped in the DVD-ROM and first ran the Windows 7 Upgrade Advisor.  I was told my fingerprint reader device driver would need to be updated.  That was fine advice expect that I already had the latest device driver (after digging into multiple PC-OEM and manufacturer websites).

Next I started the Windows 7 Install... a pretty window appeared with Windows 7 styling... promises of "Copying temporary files" appeared and then - poof - the upgrade stopped.  No warnings, no messages, no errors - nothing.  Tried again - same thing.  Reboot, try again - ditto.  Search the web for people with similar problems... nothing.  Not a satisfying first day on my way to Windows 7.

Following a good night's sleep, movie and dinner I decided to try again on the theory (guess?) that something was blocking the installer - and that perhaps removing some applications would clear the blockage.  I uninstalled a few applications I didn't use anymore and then re-started the Windows 7 installer.  Surprise surprise - my guesswork paid off and the Windows 7 installer started successfully.

After a few minutes of whirring the Windows 7 installer told me to quit the installation and remove Dell's Control Point software before continuing due to a compatibility issue.  I took that step and re-ran the Windows 7 installer.  Like my previous Windows 7 upgrade experience I was told to reboot.  Finally after the reboot the Windows 7 installer decided it was time to... actually install Windows 7.

At this point I was able to walk away and let the Windows 7 installer do its thing.  The upgrade from this point took over an hour and included multiple reboots - but worked.

The moment of truth - did my applications still work after gutting and replacing the operating system?  (Same feeling as pulling the engine out of your car, putting in a new one and then turning the key in the ignition for the first time...)

The answer was yes with some caveats - here are the issues I've experienced since the upgrade:

• Outlook 2007 inexplicably crashed for the first 30 minutes after the upgrade... and then mysteriously stopped crashing (tech theory - Outlook did a repair in the background)
• My printers work but Windows 7 has nagged me that the device drivers were bad - mysterious
• The AV software we use (major brand) has multiple compatiblity issues yet to be addressed
• The VPN software we use (major brand) doesn't support Windows 7 yet
• All taskbar shortcuts had to be recreated in the new Windows 7 taskbar layout (which is much better now that I'm used to it)

Given that it isn't October 22 yet (the official release date for Windows 7) I expect most of these issues to be addressed before or at launch.  On the balance a smooth upgrade - but I'm a techie with an advantage over the average consumer.  And yes, I like Windows 7 - the "money" features make this the most productive Windows O/S yet (specifically, the improved taskbar, Jump Lists, Aero Snap, Aero Peek - these are great).

Given two upgrade experiences with different sets of surprises I expect consumers will need expert help to go from Windows Vista to Windows 7 via the upgrade path - but it's worth it.