Presumably Picard does ride the same horse every time he uses his saddle. He'd spend more time riding on the holodeck than anywhere else, so he'd just have the computer generate the same horse model every time, wouldn't he?
Wasn't it just a leather saddle? Looked pretty much like our 21st century saddles to me. Are you suggesting the saddle intelligently calculates the horses measurements and re-shapes itself to fit? Guess it's plausible.
Most western saddles fit most horses. You just adjust the cinches.
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