I feel having a cold wallet on a seperate machine would be ideal, however would the payouts be traceable to that machine in any way?
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A "cold wallet" cannot send any funds. If the system is connected to the internet, then it is not a cold wallet.
You should store most of your bitcoins in a cold wallet. You should only store enough bitcoins on the internet connected wallet to handle a typical amount of payouts. If an abnormal amount of payouts occurs, your internet connected wallet will become empty and you will need to transfer more bitcoins from your cold wallet. This will give you a chance to review what has happened and make sure that all the payouts were legitimate before providing your users access to additional funds.