Whenever I get a support request on a free version, I respond with a courtesy link to a non-DRM APK of the pro version. Do these ad-hoc APK installs somehow link to the google play market by application ID and know to get updates, or are ad hoc installs frozen in time?
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Paid apps and managed in-app purchases are tied to the user’s Google account, so I don’t think this should work. However, if you
adb installa paid app, the Market/Play application displays it as ‘installed’, so you might get an update notification. Assuming it allows you to actually update, if your published app is using LVL, you should get an licensing error, because the app is not linked with the user’s Google account. If not, it might just work. Test it when you upgrade your app to be sure.