His "intuition" about short trips only happened after the illegal flock search, when he could see the full trip.
Driving with California plates isn't probable cause for a search.
If the cop had obtained a warrant before searching ALPR data, then the search would have been legal under this judge's standard. But the cop (a) didn't obtain that warrant, (b) probably couldn't have obtained it quickly enough to decide whether to follow her until she committed a traffic violation, and (c) probably couldn't have at all since he didn't have probable cause. The question of what level of ALPR search requires a warrant is evolving rapidly now, in response to both case law and new legislation (e.g. Connecticut SB397).
Kyle also disputes whether the ALPR search found anything that justified the detention. If the ALPR search was itself illegal then that's irrelevant though.