200-220 is what manufacturers consider optimum. 212 degrees is what the big number on your oil weight is rated at. For a 5W30, it's a 5W at 32* and a 30W at 212*. 250* is not enough to get me to increase cooling capacity. My Camaro has lived over 300 degrees since I got it in 2013, and it's been a race car since 2009. If the small cooler that I'm adding gets me down in the 250-270 range that'll make me more than happy. What you're forgetting is that hotter oil flows faster which helps it cool better. Obviously 300+ is not ideal, but it's far from an immediate death sentence. I'd get the gauges in then go from there. My 1500 does have a trans temp gauge and here in CO in the winter it barely gets over 100 with stock radiator and aux coolers. In the summer, it's 160-180 when towing. The key to keeping the trans cool is keeping the converter locked. If you're an off road guy, your best be may be an aux cooler that's not exposed to direct airflow but does have an aux fan with thermostatic switch.