I can never get the same level on the dipstick. I have even kicked around with putting a external cooler on the trans, since i push snow with it and all. I dont drive it alot in the summer, maybe 200 miles to haul firewood.
The 1st step should be to address the inconsistent dip stick readings.
Verify that you are not the cause of the variances, then on to what else could be causing this.
Vehicle parked level.
Transmission at normal operating temperature.
Transmission in neutral (wheels chocked/parking brake set)
remove dipstick and clean it off
insert the dip stick fully, the cap will fit over the tube.
wait a second then remove the stick and get your reading.
If you are noticing that the fluid mark is higher on one side of the stick than the other, I have found that the bottom side of the dip stick picks up fluid from the tube and will read higher than it is.
Now after controlling the above level check and it is still inconsistent, I would recommend a fluid and filter change.
Normal trans oil temp is usually around 200°F.
If you do put a cooler on it, you still want it to run through the radiator, especially in the winter.