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He just needs to hire 500 writers to work for you
Both of you need to manage your expectations for this site.
I think boss is looking for a solution that involves zero expenditure of time, money or resources.
5k keywords is nothing, try 50M.
"Actually worked for eBay, built out Zappos, helped out Zillow, Houzz etc.. Real Estate combos easily exceed 50M with local terms. "
it was similar to tradeindia and indiamart