Actually I don't know how the actual flag checking should be made simpler without your data structures or what you want to do with that. Basically what you have is:
if (m_pDeviceHealth->getHealth().isSet(PLAYING))
| your expression | |your flag|
Seems quite minimal to me. For different flags you'll obviously need different if branches. If you are looking for checking if any of multiple bits is set, you can use bit masking like:
if (m_pDeviceHealth->getHealth() & (PLAYING | SYNCHRONIZING))
under the assumption that getHealth is an integer.