Bending the rules of rent collection

Is it wise to accommodate tenant with special payment needs?

Q: At the rental property I manage, we always have the rent due on or before the first day of the month. Recently I had a prospective tenant sign a lease to move in on the 10th of the month. I told him I would need to collect a full month’s rent, and then in about 20 days (at the beginning of the next month) I would collect the prorated rent so that he would be on the proper cycle of paying rent at the first of each future month.

The tenant refused and explained that in every property he had lived previously, the move-in date was the date that rent was due each month.