I am experiencing the exact same issue since the last update (1.99.49.24360). However, after the new May 4th update nothing changed, and instead of happening only shortly after launch, it happens with a new playlist, so when I open a file from my media library with a 50% chance.
No error reporting gets triggered and running with /procdump or in safe mode still causes issues. Switching from Not So Direct to the WASAPI output did fix this issue, though, so I'd suggest looking into that, also because it's the best output you can choose at the moment.