Not sure how exactly Training All works, but with Enter All. You can set up Settings to enter your horses into all competitions they can long as they have the energy for it. The overall settings is under Estate: Manage: then allll the way to the right under Settings. You can have minimum and maximum amount of Entries you want your horses in; Primary or Secondary Disciplines along with options to enter for random Halter and random Shows.

I simply have mine set up for Primary Discipline. 30 entries and below and when caring for my horses, I just hit the Enter All option that shows up under the Trophy icon for each horse. It makes thing sooooo much smoother and if there are Entries over my set amount, I can easily hit Edit Settings under the same Trophy Page and change the number. It's usually for that horse and that horse only so it's not widespread.