What's the story between Wyly vs Hank & Wyly vs Jamie?

Hoping someone else can explain this too. I've seen this movie a couple times now and it never is really clarified.

A couple ideas:

Was Wyly supposed to ride Ransom originally while Hank had been working with/riding Ransom all year?

Was Jamie's horse bought by Wyly and that's where the tension came in, which is why at the end Wyly told Jamie to take the horse with him and he'd lease it out to him (or something to that effect, 'you can buy him back from me' or something along those lines)?

Jamie had some relationship with the family in the past. Why didn't he ever end up with Kyra Sedgwick's character? Always had a thing for Grace, maybe?

I'll give it a go... I believe that Hank had been training Ransom all season for Wyly to ride in the jumping competition. But then Wyly got the wild hair of buying Jamie's horse and taking that horse in the ring, negating all of Hank's work. (I'm guessing there is some money involved in winning for the trainer, aka Hank). Jamie was ticked off because Wyly didn't have a good feel for the new horse, thus causing him the championship also. So at the end, Grace decided that letting Hank take Ransom in the ring was the decent thing to do.

Also the dad knew Ransom could win and didn't want the competition. Grace allowing him to compete made it a fair competition.