I used to notice that as well. At some point, I stopped caring. I noticed that DT tends to play everything in long shows and A-Log & I are both otakus, so the songs overlapping is to be expected. In the end, it comes down to a diverse playlist and a unique delivery. Listeners might overlook my crappy microphone & mixing it with Audacity 2.12 if the presentation itself doesn't blow goats.
It doesn't hurt to have scripts using the site's own song page annotation built in. "Perform Show Research" turned out to be a useful site function. Said page annotation was virtually always written by me, so it's no big deal. And I'll often repeat what was written about a song in different shows. If listeners even notice, they don't mention it.
The gimmicks do the rest and break up the monotony. You're expecting a show about winter, then up come the Pythonesque horns and the theme breaking gimmick turns the rest of the show or segment into smashing mice with hammers or something. Yes, unpredictability = fun.
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Dave AuJus:
...Then I was half way through the second show, a 2 hour show, when other DJs started playing all my song choices.