If asking for a free upgrade is acceptable, then so is asking for free breakfast. My personal issue is framing this as a trick is that it transforms what is essentially a prerogative of the hotel to a privilege of the customer which in most cases turns sour. Do this enough and the hotels will constitute a policy that all such requests will be blanket rejected - tragedy of commons.
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Disclaimer: The content above is only the author's opinion which does not represent any position of Followin, and is not intended as, and shall not be understood or construed as, investment advice from Followin.
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