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antiall, if you want to make your dog as good as possible, just don't train him for awhile - have him continuously come in the top 4 without winning if it forces your dog to retire if he wins it all (haven't gotten that far yet). Inifinite $ = infinite skills if you ever decide to upgrade him or you will find out what the cap on skills is.
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When you retire your dog, training stamina or speed costs the same price to train the new dog as the previous one (before you retired it). Is this done purposely? It seems counterintuitive to start over but have to pay $400 to train your new dog, as opposed to $150.