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Plex seems the obvious:
Plays back original or transcoded depending what you choose in settings;
Supports podcasts and chromecasts;
Allows multiple libraries;
Has an app on pretty much every device out there which works locally or remotely (and allows syncing for offline play as well).FLACs aren't stored in the cloud but they can be accessed from anywhere so I don't think it makes much difference unless you have poor internet at home. If you really want a cloud solution you can set up Plex on AWS or Digital Ocean or something but it would probably work out pricier than a local solution.
following up from last post, there really is no good options for music on the go for people with their own libraries. maybe im a niche market.
how is this so hard?!