shouldSkip used to execute correctly when you clicked next. It would first get the ID of the next guider, then see if skipping was needed. See https://git.wikimedia.org/blob/mediawiki%2Fextensions%2FGuidedTour.git/40e856360e4ba377242c172b036477aebf740ad9/modules%2Fmediawiki.libs.guiders%2Fmediawiki.libs.guiders.js#L774 .
The same should happen with transition, but now it works for neither legacy shouldSkip nor AFAICT transition.
For an example of the regression on legacy, try going to https://en.wikipedia.org/wiki/Wikipedia:TWA/1/Start?tour=twa1&step=6 then click next.
There is a shouldSkip on step 7 (the one you hit when you click next):
shouldSkip: function () { return mw.config.get( 'wgUserId' ) !== null; }
Thus, it should automatically skip step 7, since you're logged in. However, this doesn't work.