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I've noticed some tags bear a logo. It would be nice to have the R logo on the tag as well. Is this doable / legal?
Tags have logos if they've been sponsored by companies (see the faq entry). If you want to pay them to add a particular logo you can (see Ad Sales and Sponsorships), but I doubt they'll do it for free since it's one of the ways SO makes money
Logos on tags mean that they're sponsored tags. Shoot some cash over to the team and I'm sure they'll be happy to put the logo on.