Troubleshoot upgrade of paid app
As you have ADB available to use, here's one proposed way:


Make a backup of your current installation (app and data):

adb backup -f osmand.ab -apk net.osmand.plus

Same, data only

adb backup -f osmand-data.ab -noapk net.osmand.plus

Uninstall the app (.apk) while keeping its data:

adb uninstall -k net.osmand.plus

Install the new version from play


If the last step succeeds, you're done and the new version should be installed and working. Otherwise, repeat step #3 without the -k switch, then step #4 again, and finally restore the data from your second backup:

adb restore osmand-data.ab


If that should fail as well, just restore the first (full) backup to get back to where you are now. But I'm pretty confident at least the second run will work out fine.