Okay, I may have found at least one way to work around this, but it requires a MobileMe account.

Don't ask me why, but it occurred to me that the MobileMe Contacts web application might do a better job with the file formats that include transparency info, so I checked it out and sure enough, one of the options it accepts for upload-able Contact's image files is PNG. So, I saved my TIFF as a PNG, preserving the Alpha channel, and uploaded that. After the next MobileMe sync on my computer, my image for my "My Card" in Address Book now displays with transparency, and, more importantly, so does my user icon in the login panel and Fast User Switching menu!!!

Unfortunately, MobileMe web apps are really acting up tonight (anybody else noticing that?) so I can't check it out more rigorously right now, but I thought I ought to get a correction up here with as much as I know for now… maybe this could have been accomplished without using MobileMe, simply by importing the PNG version directly into Address Book on my computer (though I did try that using the TIFF with no success, so I'm a little skeptical of the chances…)

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