Simple; the MC makes good on saying he'd climb up to her balcony because she avoids throughout Ep 7 and Jill is so taken by this gesture that she finally gives in because it's the most romantic thing anyone has ever done for her. It's also very "Romeo and Juliet" as, setting aside how that story ends, it was a measure of how much Romeo loved Juliet that he would risk so much for her in that story, and this would be the MC risking a lot for Jill.
I honestly think this is the best way to break down Jill's defenses completely.
This was definitely more than than a "lighting issue". The images are labeled in the game files as "surprise" and there are 2 images where 2 lights appear to be obstructed by something in front of them.
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On one in particular, by increasing the brightness and contrast, it would appear to be a person blocking the light.
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So really the question is, who is this and what were they sneaking around for? Also, if this person was sneaking around here, perhaps they were also sneaking around when he was with Bella and it could come back to bite him.
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