Some higher RPMs wouldnt hurt, as you are a hair above the factory stall speed. Read- not in the transmission's best efficiency range. I'd think 2200rpm would be better for long hills- get more power through the transmission and not produce as much heat per power transfer. Your engine certainly has room to grow, unless your t-couple is in the pipe, in which case you are probably pushing the limits.
The stock cooler is pitifully small- a tiny deal in the upper left corner of the radiator area. I'd put a bigger one in there if upping your engine RPMs doesnt help.
Third option would be a tighter converter. How much does your trailer weigh? I'd think you'd be able to go faster than 30mph up a 5% grade, even with a stock engine, unless your transmission temp is your limiting factor, which is good on your part.
Daniel