Second -- we run 2 printers off the "server" in present setup. I can't find anywhere whether printers can be connected to the Server under SBS Essentials, or whether I am going to have to have another machine to be the printer server.
SBS 2011 can share printers easily. A print server is something different which Windows 7 can not do, but SBS 2011 can. Then again Print Servers serve little benefit in a small office environment. Basically, yes you can share printers no problem.