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I've never regretted buying a pony, but I've regretted paying too much for said ponies. It's one of Murphy's Laws though, isn't it? No matter how long or hard you shop for an item, as soon as you buy it you'll find it on sale somewhere else for a better price. Happens more often than not, I'm afraid!
But REALLY -- more than that-- it's all the little $1-5 ponies that I bought because "pony".. I felt like I was drowning in ponies, they were hard to sell, and that just adds up. That bothers me way more.