Ok so one plan for multiple domains each for their own site.
You can only set up additional domains for a single site. So if you have multiple domains for a site, you can set one to be the primary domain while others will redirect to the primary domain.
example, one account upgraded to business for 5 different sites each has own domain?
You can only upgrade a site under an account not the entire account. You can have different sites under one account with different plans. Each plan for a particular site is independent of the others. So if you have five different sites, you will need a plan for each of them in order to have a custom domain.
Let me know if you need further assistance.
Source: Wordpress Upgrade for Multiple Domains
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