As far as shipping goes it seems to be working correctly. If you ship a horse 1/3 to a track and it says it will arrive 1/3. I am assuming you’ll be able to train 1/4, and it won’t show at the track until 1/4. I don’t train horses but working a horse the day he arrives at a track doesn’t make sense. You let him calm down and adjust I would think. Dam 
this is going to drive me nuts. Fun though 
All of your 2yos are still in transit, which is why they cannot be trained. All of your horses can ship places besides Arlington.