Dedicated proxy hosting

If you run, lets say hundreds of proxies, would it be better if you bought your own servers and host them rather than just get a hosting service? Wouldn't it be cheaper in the long term?

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definetly!
you don't need hundreds to buy 1.
if you've got 10 for example with excellent traffic, you should start thinking of getting 1

who owns 100 proxies?
largest networks i know have about 20 or so proxies

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yes proxys do consume a lot of bandwidth, so becomes nessessary to own a server rather than depending on others.