ctypes makes it really easy to control the USB-1024HLS Digital I/O box from python.

This gets the 2 functions I need and tests to see if the device is there

import ctypes
UL = ctypes.windll.cbw32
cbDConfigPort = UL.cbDConfigPort
cbDOut = UL.cbDOut

FIRSTPORTA = 10
FIRSTPORTB = 11
FIRSTPORTCL = 12
FIRSTPORTCH = 13
DIGITALOUT = 1
DIGITALIN  =  2

port = FIRSTPORTA

try:
    assert cbDConfigPort(0, port, DIGITALOUT) == 0
except AssertionError:
    print 'Configuration of the USB-1024HLS failed'

Then to send data, I simply

cbDOut(0, port, bits)