My understanding is that all you need to do is make sure your app is signed by your market key and it's version code is lower than the update you'd release on the market next and those people will get a proper update from the market. This really shouldnt be an issue. Ive done this on my android phones.
No. This doesn't work. At least not for the Humble Bundle games. The market shows an update available for Osmos, but when I click the update button it says it couldn't download the update because I haven't purchased the app.