A little frustrated and confused that my level one rider still isn't leveling up. I've been regularly training her unless it's a show entering thing.

I don't know what level riders you have, but the higher their level, the more training they are going to need. For example, a Level 1 rider may need, say, 4 weeks of training to level up, but a Level 8 rider might need 14 weeks to level up (just pulling those numbers out of thin air, I don't know how long it actually takes on average for them to level up).

Other than that I'm not sure why they would be taking a while to level up.