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[Spud&Saf]

It sounds like he is just confused by the difference in rider positions from a hunter versus dressage rider and needs to get used to adjusting within...

[Spud&Saf]

The first choices I would look at for that back would be something like an Albion or Black Country. These English made saddles come wider, have options...

[Spud&Saf]

I have the Tipperary Royal wide brim, it has a dial. I love it!

[Spud&Saf]

In your budget (new), the Thornhill Germania Spring jump saddle may work. You may also find a forward flapped Prestige or Childrec used in that range....