Ever had that clip that was gold but obviously does not loop? It doesnt work as a ping pong and you dont want to loop it as the jump is obvious.
My suggestion is a new play mode that crossfades the end of a clip with the start of itself. Its like loop, but just crossfades X frames before the end into the starting x frames.
Attached is an example of where it might go and how it integrates into your already exceptional software. It needs a snazzy hipster name, but you get the idea.