I am not sure that I get things together here. First of all, having the databases trustworthy is not going to help, but it is a possible security risk.
You say:
Linked Server connection created (Mapped LocalSQLUser to > RemoteDomainUser, With all connections using current login's security context)
This is kind of contradictory. Have you set up login-mapping, or are you relying on self-mapping? I realise that you talk from the UI, but the UI is more confusing than useful. Please use the scripting button in the UI and post the script, so we can see how the server is set up. If you mask actual data, please make sure that you do it consistently.
If you have self-mapping, this means that you log in on the remote server as yourself. You cannot do EXECUTE AS to impersonate a different login and access the other server with that login. The impersonation you do is only valid in your own SQL Server, but not in Windows or any remote data sources - that would be a major security hole, as that you would permit you to impersonate an admin to elevate your permissions.
If you have set up a login mapping for a specific login, you can impersonate that login, but I stop here, until I understand your configuration better.