When using stills to simulate videos in demo workspaces, give the stills a duration.
In the timeline group you can put the start cue in the timeline group itself.
If the timeline group loop fails, it's because the start cue is still technically running when the group restarts. To fix this put a 0.01s pre wait on the group (or set the group to 'on second trigger hard stop and restart in the triggers tab.
If you are using a Start first child group, then for this case you would want to use the 'and go to next cue 'variant, as presumably the next time you hit the go you would want something else to happen.
If your stills have duration, to simulate video files, then you can use auto continues with negative post waits to overlap them to allow for your fades
In this instance you don't need fade cues; you can just set all video cues to bottom layer, and select fade and stop peers in x seconds in the triggers tab.
In this screenshot:
Basics Tab:
Stills set to duration of 3 secs (to simulate videos of 3 secs duration.)
Video cues set to auto continue with a prewait of -1 sec, i.e the next cue will start 1 second before the end of the cue, this is precalculated which is why the inspector shows a post wait of -1s and the cue list shows a post wait of 2s (3s-1s)
Triggers tab
Video Cues set to fade and stop peers in 1 second.
Geometry tab:
Video Cues set to bottom layer.
Screen recording attached of final result.
Does this do what you want?
Mic