im willing to bet you could get a bluetooth obd2 sensor, and download torque if you have an android device and monitor your trans temps that way. I used to have a 2001 dodge ram van 2500, would monitor trans temps constantly. it was our band's van, we toured all over the US in it, towing a 5x10 everywhere loaded to the brim.
you DON'T want to tow without pressing that OD Off button. I know there is a little bit of conjecture in this thread, but i can tell ya it's not great if you constantly allow the trans to enter overdrive and come out all the time. that generates a TON of heat, and too much heat is the enemy of any transmission. remember this:
engines like to be hot, transmissions like to be cool.
i bought a 1995 b2500 ram van before we had our 2001, and immediately had to rebuild the transmission due to the TC taking a dump.
paid $2500 for the van, $1900 for the trans rebuild. Transmission ended up dying on us in Springfield MO because some of the other guys didn't like to pay attention to OD/trans temps. We left it in Springfield.
If you have to question whether you should be in OD or not, it's best to just leave it off every time. Check the fluid in the trans, and change it if it smells burnt. The fluid broke down too much if so, and won't be properly lubricating the valve body like it should.
here's a pic of the 01, the church special haha