This very well may be a stupid question but I was wondering if there were any issues in “upgrading” from free accounts to premium or family versions? Like, how hard is the migration?
Thanks.
It is pretty seamless, but let us know if you have any specific questions and feel free to contact the official support team at https://bitwarden.com/contact/ Here is a free to org (family) guide for example: https://bitwarden.com/help/upgrade-from-individual-to-org/
Thank you for the response. The issue is that when I go to account settings, I don’t see the option to upgrade to a family plan. So I want to make sure I can upgrade my and my wife’s accounts to use a family plan. Sorry if I’m confusing things.
Thanks.
The team is working on improving the visibility, be sure to use the contact link above if you need any help from the support team 
In order to upgrade an existing 2-person Free Organization to a premium Families plan the FAQs section here details this.
I would also note the section as mentioned, you will need Owner level access to change this.
You must be an owner to update billing information for your organization.
I have also created a quick guide to detail the process currently.
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Navigate to the Bitwarden web-vault and log in.
Select the Organizations tab to view your existing org.
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Under the appropriate free Org you wish to upgrade, select the Billing tab.
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As directed in the help article Update billing information for organizations, you will need to add a payment method to the Organization, or add a credit as available under the Payment Methods option.
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After either a payment method has been added, or an appropriate credit has been applied to the Organization you can proceed back to the Subscription option to then Upgrade plan.
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Select the appropriate Families (or business plans) for your upgrade.
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Confirm and select Submit.
You should be successfully upgraded!
If there are any errors you can reach out here, or contact Bitwarden’s billing team directly for further support.