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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

So... does the story end after your horse reaches level 10? Anyone know? The last quest I get is to talk to Robbie and then you get to start over with a new horse. Then afterwards the game just sets you free with no further directions. Talk about feeling majorly incomplete....

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...