I'm not seeing this specific example answered so I'll put it here.
If I have 2 RDS VMs running in 1 location and I have user CALs but users will likely be connecting to both machines at the same time, will I need 2 licenses for each user?
will I need 2 licenses for each user?
No. Per user licensing is per user, not per user per server. It doesn't matter which server they connect to.