Most of the training kennels I've seen have their titles as "Grand Master Trainer" which is well, indicative of that 100 in training. xD
I've also had breeders that have 100 in skill, but aren't efficient as well with sponsor trainers.
I'd rather …
If they haven't been entered in any previously, then you can enter them into four events max when they're in a boarding kennel.
You could always just reclaim the dog, take a turn, put into boarding kennel, and enter four more events though.