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Sounds great from a marketing perspective, but I need to understand if this in any way will affect my reputation with Search Engines. Will it set off any Black Hat red flags? Will it diminish the ranking of PrimarySite.com? I don't care about and SEO issues with ContestSite.com.
Thank you.
I would agree with just going with PrimarySite.com/contest.
If you set up a 301 redirect from ContestSite.com to PrimarySite.com/contest, I don't see any blackhat issues there (assuming that ContestSite.com isn't banned from search engines for spamming or something unusual like that).
The domain ContestSite.com will probably never rank in search engines, if you show up in search results, it will be PrimarySite.com/contest that will show up.
You get the thumbs up from me.