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Transferring an active site to a team

I’m trying to try an actively hosted site to a team but it says I need to cancel my plan first. So I have to cancel my plan, transfer the site, then re-purchase a new hosting plan? Is there a way to transfer sites to a team without the site going offline?

No. The site would only be down for as long as it takes you to do it. Seek a credit from support once done.