Heat is what generally kills these transmissions. The first, and most important thing you need is a transmision oil temp guage.
Assuming that you are hauling something 5,000 lbs or less the transmission should last indefinately if you keep the temps under 200 df. Cooler is better in this case. Transmission life is dependent on the lubricant temp and repaidly decreases as the temperatures rise.
For heavier loads a seperate cooler may need to be installed to keep temperatures in check. The 727 transmission is a very fine one, though a dated design. Yes, you are correct that the Cummins can stretch it to it's limits especially if you are pulling big loads.