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I think you will know instinctively when its time to change your gear. I like to do it before the old gear drops too much in second hand value and is still popular enough to sell quickly. Buyers of used equipment are not just looking for a bargain, they want to know if their purchase is going to be well worth the dosh they are parting with too. Like most people, I need to use whatever money I can get for my old gear as part of the new purchase, so I try and time it to the point where it won't cost me an arm and a leg to do so. I recently sold my EOS 5d in mint/perfect condition at the high end price of £800, which went a long way to purchase the MKII with my small budget to add to it.
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