Machine A needs to log into machine B from offsite via internet, no problem, I can do that.
Is it possible or is there a setting to allow an application on Machine B to print to a printer connected to machine A. Alternately if there is a (free/inexpensive/not beyond the skills of the average tech to install) 3rd part app that allows it.
In the properties of the client software on machine A, (microsoft terminal server client or MSTSC) there is a tab that allows you to share resources, disk drives, ports and of course, printers. Give it a try.