I work with Ableton Live 9 (9.5 now), as well as Pro Tools and I've run into the occasional "drop out of sync" in both when loading a plugin during playback or enabling/disabling a plugin etc.
As a rule I never load instances of plugins or effects of any sort or enable/disable them during playback (especially when a plugin or proecessor is known for increasing buffer/latency due to lookahead or needing a larger buffer than playback is currently set at).
I don't find it the least bit bothersome to simply stop and restart the playback to get things back in sync. I will add that there are times when things just didn't seem to want to allow me to track/record with input echo in-time even with just a single ProChannel EQ enabled on a single track without causing noticeable input echo delay for monitoring through FX. I haven't run into that situation often but it certain can be a session stopper when it happens and my clients rely on hearing themselves through FX to perform properly.
The most recent occurrence of any sort of beat-sync oddity I've been running into is during tempo changes when using Kontakt 5 with tempo-sync'd instruments and triggering at the right tempo. In these cases I have at least been able to workaround the issue by going into the instrument settings within kontakt and forcing manual tempo to the proper tempo I need it to be at.