When the debugger is attached to a process on remote server -
What locations are searched for the pdb? In what order? (e.g. is it searched on the remote server (debuggee) or on the local client (debugger))
When I use the debugger to manually load pdb file from specific location - is the debugger looking for the file locally or is it the remote debugger monitor looking for the file on the?
Is there any article that describes that process?
The machine the debugger is running on loads the symbols (not the remote).
This article explains the basics of setting up where VS looks for symbols:
This one explains how to set up a symbol server in the search path (which is particularly useful for Windows symbols):
There are a lot of pitfalls for remote debugging (mainly having to do with connectivity and permissions/authentication). See the following page for a list of links that you'll want to read up for details: