We made two trips moving them 2-3 miles using only one deck on the trailor. The travel was no longer than 15mins, I wouldn't have thought it was too stressful
Um... is that 23 ewes on one deck? Unless it's a very very large trailer, or they're very very small ewes, they'd have been fairly packed in? Or did you mean 23 ewes across two decks, twice?
However stressful or otherwise the journey, or whatever other stress (could've had a hot air balloon going over, a pack of hounds running through - all kinds of events can cause some ewes to not implant or lose an embryo), any kind of problem would, as others have said, not usually make
every one not hold.
However, if he's only a few days into the second cycle, I would just give it a few more days. When an inexperieced tup goes in, he may mark quite a lot of bottoms he hasn't fully and successfully serviced, so you may get quite a few apparent repeats for the first few days of the second cycle. But if it doesn't settle down, then definitely get another tup on the girls and either get this boy tested or send him down the road.