While researching this issue, I found multiple mentions of the following scenario online, invariably as unanswered questions on programming forums. I hope that posting this here
The first thing that I'd do would be to check the return values from the waveOutX functions. If any of them fail - which isn't unreasonable given the scenario you describe - and you carry on regardless then it isn't surprising that things start to go wrong. My guess would be that waveOutWrite is returning MMSYSERR_NOMEM at some point.