I don't think it is possible nor is their an app for it to show you immediately , an app update is available
As far as I know , The Market periodically checks for app updates and if it finds any , thats when the Icon appears. I think I have worked out for me {UK}, The app's are checked around 23:30 GMT every night , Once every 24 hours. I could be wrong but this is what I have noticed. Some days I wake up and their is updates but I'm not notified at all.........
There is an app called aTrackDog that will follow the udates for you and even follow apps that have been deleted from your phone if you wish to do that.
I just got an update today for the App WHERE...I looked at my Droid and up in the Notifications toolbar I saw an icon of a little shopping bag (looked like the Android Market Icon) and it said Update for WHERE available ...clicked on that and brought me right to the update...downloaded and updated fine...Ive never seen that update notification before...but there it was this morning
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