#1 I figured it out -- it won't accept anything other than "yes mistress" w/o the quotes -- meaning no commas (and i don't recall if i put a period or not.) -- random bug happened -- met Jennifer at her apartment and she told me to follow her, I had to call her to get the next steps to trigger.
#2 makes more sense now, thanks!
#3 I feel like she shouldn't just give 2 chances -- she should be exasperated, but offer a third chance with a bigger challenge, imho, before giving up on MC entirely.
#4 Wasn't sure if you were aware, also I do wanna advise that this glitch happens quite randomly. I didn't notice any commonality or reasoning why, it'd just disappear.