So at least they know about and acknowledge it. There is hope!The behaviour that you've observed is indeed a bug which we are aware of:
"Playback from insert marker doesn't work in multi clip mode [Option Space(Mac)/ Ctrl Space (Win)]"
I am adding your case to the bug ticket and placing it into the "on-hold" state. Although I can't know when or if there will be a resolution to this bug, should there be an update, you will receive notification directly in this thread.
Play button always start at the beginning
Re: Play button always start at the beginning
OK so Ableton support have just replied: