I only use cruise control on flat sections of highway. When hills come, I turn the cruise control off because I want to control when I get the transmission to kick down to maintain my speed. What I've noticed is the cruise control system can get the engine to race with higher rpms than I would have allowed to happen when I "ease" it into the downshift rather than slam it into the downshift like the cruise control can cause.
When hills become steady, overdrive always is turned off and remains off until the road flattens out again and my speed increases. Turning overdrive off can lower your trans temps a fair amount, 20+ degrees, when you're at the speed between around 40 mph and 60 mph, basically in that area between 3rd gear and overdrive. Overdrive off locks up the torque converter reducing the heat generated in the transmission.
The video below isn't the clearest but if you watch my phone carefully, you will see how turning overdrive off can lower your trans temp.
<iframe width="560" height="315" src="https://www.youtube.com/embed/BEZfDOkGVno" frameborder="0" allow="accelerometer; autoplay; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe>
If you regularly drive in the mountains, I highly suggest you install an external trans cooler to help keep your trans temp down.
<iframe width="560" height="315" src="https://www.youtube.com/embed/2nVbwe2t2T8" frameborder="0" allow="accelerometer; autoplay; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe>
I also highly recommend you start monitoring your trans temp. Since you have a 1998, you can't monitor your temps by pulling info via a scan gauge or OBD II reader sending info to a phone app like Torque Pro. You will need to install an aftermarket gauge like I did on my 98.
<iframe width="560" height="315" src="https://www.youtube.com/embed/fT_2szdKXRM" frameborder="0" allow="accelerometer; autoplay; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe>
When 4wheeling, knowing when to switch into 4Lo can also make a huge difference in your trans temp. Anytime the trail starts to climb consistently and my speed is pretty slow, 20 mph or less, I put my transfer case in 4Lo. The difference between 2wd or 4Hi and 4Lo can be huge. In 2wd or 4hi, I could get my trans temp to get into the mid 200's or higher on a sustained grade. As soon as I switch into 4Lo and just resign myself to driving slower, my trans temp will drop to the sweet spot in the 170's. People that don't understand this and don't monitor their trans temps are the ones that will get the trans temp "idiot" to light up on their dash letting them know they cooked their ATF. That light supposedly lights up when your ATF hits 300 degrees. At that point, your ATF is cooked and a prompt flush is in order.
<iframe width="560" height="315" src="https://www.youtube.com/embed/wqxeZvljYGc" frameborder="0" allow="accelerometer; autoplay; encrypted-media; gyroscope; picture-in-picture" allowfullscreen></iframe>
Heat is the big killer of automatic transmissions and ignorance definitely isn't bliss if it's going to cause you to burn up your transmission. Even with a trans cooler and turning overdrive off, you can still overheat your transmission. Sometimes it's prudent to pull over and give your engine and transmission a break when temps begin to spike. I did this when I was traveling up a brutally steep and sustained road in Death Valley. Better to pull over and let things cool down rather than overheat your engine or trans.