My company is running two Exchange 2000 Server machines in one site. Can I create more than one SMTP connector and have both boxes send email externally?

Yes. By default, each server's SMTP service can send email externally, even if you change the default configuration. Because the two servers are in the same routing group, they can route mail between themselves as necessary. If you want to consolidate mail routing, set an address space and connector options to create an SMTP connector on either server (or both) and control its behavior.