Yeah, the timing would be close to present day, where Rider and the end of Mentor were about a year ago. Kayla hinted at the end of Mentor that finding out about Michelle's past had gone a long way toward them reconciling, since she felt Michelle's wife had been an abuser.
I did like Anita's comment about what happened the last time Kayla and Michelle had gone drinking together... 🙂
Also, the Special Guest Star did show up one time outside of her introduction. It was in Caffeine, but she wasn't named. I think that's been mentioned before.