With the 2nd gen 1500's it is NOT a good idea to drive with O/D on if you have anything heavier than 500 pounds in the bed or in tow. Most reputable transmission builders will tell you to turn your O/D off while in town. The overdrive module in our 46RE trannys are one of the main weak points. You will not burn any more gas with O/D on as long as you keep it around 45mph. The engine will maintain speed easier and won't be under load as much when you have o/d on (Which also makes the transmission happy by keeping it cooler). The ONLY time I use O/D is when I am traveling 55mph+.
And Adam, it is much peppier with O/D off. The O/D (4th) gear ratio is 0.69. If you have the standard 3.55 axle that is only a 2.45 final drive ratio! (Gutless).
3rd gen guys, throw all this out the window. But, you should still use Tow/Haul with anything over 500 pounds.
I would rather pay a little more for gas than 1500-2000 for a new Tranny. And lets face it, in the 90's, Dodge was not known for its superior transmissions!