#1 is correct. TS is a little different than Citrix. I has both systems in my network. Citrix was able to print as you both said. :) Well, regarding your question. You can try to share your boss printer and make it accessible from your LAN but this will be difficult because of WAN, dynamic addresses, and traffic will go twice - forth and back. Other choice - client side. exact as in article you mentioned. You need to start terminal session from boss computer, login as administrator or as boss (if he has rights to add printers), then you install printer on Terminal Server through it, as described in article. you need to select "Local Port", next screen will show you "Use following Port". Here should be lines like TS001, TS002 etc up to TS012 (in my case). There is description for each port - which machine and LPT is mapped for this TSxxx. You check appropriate port and see result. If you can't select "Local Port" or to find port mapping you can do this later. There is tab "Port" in printer properties. Phrase "Inactive TS Port" means that no Terminal Sessions which provided printer for this TSxxx connection. And WAN sessions shouldn't provide port for Server so it most likely you won't see your boss printer here. try to connect notebook to LAN, do all the same and compare - will you see your port?
There is another article, by the way:
support.microsoft.com/support/kb/articles/Q238/8/41.ASP
But it still about LAN...