Is it possible to have 2 people logged in separately at the same time using same login or do we need 2 coaches set up and logged in separately to do this?

You can have two people logged into the same system at the same time.  This works perfectly for the purpose of administrative support helping a coach manage their system.  If however you desire two coaches to be using the same system, that would cause problems. While two coaches can technically be logged into the same system both coaches would be using the same client list and scheduling client appointments on the same calendar. The Console calendar only allows one appointment per slot on the calendar (therefore coaches couldn’t schedule two appointments at the same time on the calendar). 

So for the purposes of Admin and VA support, yes two people can log in and be working inside the same system.  For more than one coach accessing the system, I would recommend having an individual system for each coach.

Note for caution: If two people work on administrative tasks in the system (editing pages, doing update, saving, etc.), there is a risk where, if they are both working on the same thing (same location in the system) at the same time, they could overwrite each others actions in that location.