Thank you both for the info, even if it is bad news.
Originally Posted by RUBI 4 MY MRS
To start off, when you do the on-off thing you DON”T hold the reset button to get the codes. Now the bad news, on some yrs that feature doesn’t work & I think 2000 is one of them. Try it to see. Check the OBD port contacts. See if there is corrosion or anything that may be causing the scanner to not connect.
Prior to attempting to run a diagnostics test using the odo reset, I did try the turning the key to on three times without any other steps. As you surmise, this did nothing except turn the dash on.
OBD port contacts look good, even with 200 lumens shining on them. The scanner did turn on the moment I plugged it in as well.
Looks like I'll be making a trip to the Jeep dealership.