Hi,
Based on my knowledge, unfortunately this is not possible since the user B email address is the same domain and the autodiscover/EWS query will be done within the domain and will not check for the availability address space.
May be we look for options like (if any), real time sync between office 365 mailbox calendar and external calendar for user B, so when user A check in scheduling assistant, it will fetch the free busy information from user B's office 365 mailbox calendar which has the updated information from external. Another option, if that external system supports option like sharing calendars, then User B's external system calendar can be shared with User A and sync. However, if the user A still uses scheduling assistant then the free busy will be retrieved from the User B's office 365 mailbox only.