Once the analog dispatch unkeys, the scanner will move to the next channel (frequency) programmed, which in this case would be the digital version of the channel. So, if the mobile replies in digital, then you'd hear it. Then, once the digital (mobile) quits transmitting, the scanner would then check for the next active channel. Depending on what else you have loaded, it would then pass back to the analog channel again when it comes up in sequence. I'd also suggest not using a delay over 1 second, since apparently they are swapping modes back & forth.
Once or twice a month, I visit a friend at her place in a rural county, about 100 miles west.
Stephens County is set up much the same as yours. While you do not have a system hold option on the WS1065, I do on the Uniden scanners, so for counties like this, I add a one or two second hold, to keep the scanner looking at that system for replies alternating between analog and digital.
Texas DPS is much the same. I use a system hold on it as well, since the base and mobiles are often on separate frequencies (not repeated).