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I don't think there is really anything problematic about this - pony (and cart) and Shank's pony were the normal methods of Shire transport as they were in England in Tolkien's youth and a while longer (we just met up with a distant cousin and my Dad was reminiscing about going on her father's milkround in the thirties and that was with pony & trap). None of the hobbits say "oh but I can't ride..." ..even Sam.. he would have been used to the ponies used by his farming connections. We know that farmers such as Maggot have working ponies and I imagine that wealthy hobbits such as Merry and Pippin had riding ponies for fun especially if they lived in rural areas.
Brandy Hall had over a hundred residents at any given time I think. I should imagine that there were probably a fair number of ponies available anyway (rather like a modern car pool). I don't imagine anyone would have batted an eyelid if Mr Merry or Mr Pippin had bought a pony or two extra -anymore than we are suprised if the modern rich have more than one car.
The only reason there were problems getting ponies at Bree was because they had all been driven off. I don't think for a moment that there was a general shortage.
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