You should not be clearing the session anywhere except for logouts. The multiple characters problem would be easy to solve if you sent the character ID in each request and used a corresponding key to store in the session. For instance your URL to play could be mygame.com/play/character_id You could also just try and send the character id with every request and reading and writing from the database every request, it may be fast enough, databases are really smart about caching nowadays so you may be prematurely optimizing something that doesn't need it.
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