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I'm not having luck putting a saddle on... HELP? Am I doing something wrong or is it a glitch? THX

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I've got to the quest where I need to beat Eddie's time to get his tools on two different game saves. I've went the way the game directed me to (no timer on screen now) and have looked all over the area, but yet I couldn't find his tools anywhere. Does anyone know where they are/how to progress in the quest?...

Unless I'm doing something to CAUSE this illness? My Horse was healed by the vet for free when we met, then when i left was sick. I assumed it gave me medicine but I saw nothing in my inventory, turned around went back to the vet and the animal had THREE separate illnesses that needed to be cured for $100 or so each. About 5 minutes after leaving the vet, my animal turned up sick AGAIN. OK fine. I fix it. Went and did a task. My animal. Was. Sick. Again. By my count, if you exclude the initial one tha...