The fact that some contests limit you to three entries, to give a recent example, indicates to me that the other contests do not limit you.
I have often sent in as many as eight or nine entries, and it doesn't seem to affect the outcome. Indeed, when (as is usually the case) I do not win after I send in a lot of entries, I tend to get an honorable mention, which I interpret as a nod to my effort if not my quality.
The one thing I don't think is a good idea is to get real people to misrepresent that they are the author of your entry and to have them receive checks and forward the prize to you. A pseudonym is one thing, but lying about authorship and laundering money is another.
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