That chart can be a little deceiving. Keep in mind that is the approximate length of time the trans would last if you ran it at that consistent temperature non-stop. Just because the temp spikes to 250 for a minute or two here and there doesn't mean the transmission life is suddenly decreases to 20,000 miles.
Generally, rather short spikes (like pulling a grade) do not cause long-term issues up to a certain temperature. Sure, the fluid can start to break-down at certain temps. but it does take a little while. If you are seeing these issue then change the fluid and everything should be good to go. Of course there is a temp you can get to that will start causing permament damage to the seals and clutches even at short spikes.......but it's not like the trans will be running at 160 and suddenly spike to 300 in a heartbeat, if you hit 300 than it's likely been running pretty hot for quite awhile anyway.