Money can always be a sensitive situation... I wonder if someone (you) just took charge of collecting the rent from them it would work better? I'm one of those who waits til the last day because I always feel too lazy to walk the rent check all the way over to the office (especially when it's really cold outside!). So maybe if you got all the money from them first and then took charge of walking it over, they may be more agreeable of that. At that point for them it's just a matter of sitting down and writing a check.
Especially since they're technically still not late on the rent by turning it in on the last day, they may not see any incentive or real reason to turn it in earlier. If you alleviate the burden of walking it over they may go for it. Just a thought anyway!



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