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I was able to resolve this for myself by waiting until the team in question was not signed up for (nor participating in) any tournaments or drafts.
uploaded the logo at that time, hit submit, waited a sim cycle, then started rejoining tournaments and haven't had issues since.
I don't think this is the only reason some people are having problems with logos, but it did resolve whatever issue *I* was having, maybe it'll help you out too
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