Yeah you can't avoid the rent paying thing. I'm gonna have to think about how to handle a scenario like this. I'll fix it in the next update. Sorry about that.
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Yep, but there's a problem with that method. If you try to send him a love letter again, it will lower his 'Sexual Interest' and you have to do the blackmailing thing again in order to raise the 'Sexual Interest'. And if you get stuck without funds and a low 'Sexual Interest' on that Rent screen, you're cooked pretty much. It's getting fixed in tomorrow's update though.