So for this topic, I have been thinking long and hard about. I decided that I won't be showing this fall, but I will show in the spring. This way, I don't need to worry about how much money I'll need all the time since college is just starting and I am getting my book stipend. Also, once I get more money from my college books, babysitting and/or pet sitting, I may invest in a Bates saddle as well as a bridle and martingale if I decide to lease Hercules. Also, by not showing this fall, I can get more familiar with his gates and such and become more balanced. It's better to become more prepared rather than to rush into it.
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