For what it's worth it's been pretty painless on my side, even with the beta versions. Unzip, move and restart service worked every time, even with ~7000 songs in the database.
I have been running SS on a windows server for years and not once did I have a failure with upgrades. With 50,000 songs in db - always quick and painless. I don't do anything special so the installer must be shutting things down gracefully.