I know exactly what you are doing. I am doing it.
Using Loopback will not work. You need a crossover RS232 serial link cable(some call it null modem cable. Pin 1,2,3,6 to Pin 1,3,2,6 on 9 or 25 pin DIN connectors) and connect serial port( some call it com1: com2: symbol "1010"). Configure first in Control Panel/Ports, use default ioport and irq, set to highest possible baud rate. Pretend you are installing a modem, Configure a Modem in Control Panel and you will find a Direct connect cable. Do these on both machines. Try configure a dial-up and select the dummy modem, select the highest baudrate, iff you have 16550 UART with most builtin motherboards. You may have to lower speed if found error because of distance. You may run this100 ft with properly shielded Cat3 STP cables. Remember to install Remote Access Services on the Network/Service tab and on the RAS property/configure, select appropriately which "dial" in/out simply select Both in and out.
Remember this connection is painfully slow and use it occasionally for file transfer and resources sharing(you can stack both NETBEUI and TCP/IP)
If you run W2K, you can also use parallel printer cable. I assume you want no internal installation such as NIC nor softwares such as laplink. So this is it, a poor man's link.
Good luck