Hmmm.... I believe it's still late-July on the story. Comiket takes place on early August (Aug 3rd, IIRC), so there's still plenty of time until late-September (CTMEOY takes place from Sep. 18th to Sep 25th), basically still two months to go. But.... There's something else bothering me....
Doesn't anyone remember this same "paying off Hayate's debt" story from somewhere else?
Does the name Suzune Ayasaki ring any bells?
I can't help but think this is getting a liiiiiiittle bit repetitive.