I think there is a common misunderstanding regarding how play/skip works in relation to pattern/track length.
If you have an one bar loop, and you set conditions like play 1|skip 1, the pattern will not automaticall grow to a two bar loop. You’ll have to actually make your pattern at least two bars long i.e. make any track in your pattern last for two bars (but not the one with play/skip!).
From the manual:
The overall pattern length is determined by the longest track length.
You can refer to this discussion for more info
It mentions ‘export’ in the title, but the question actually makes sense for playback too.