We have always been first of month rather than anniversary, and it sure seems to me that anniversary is a lot of unnecessary hassle. We send out bills on the 23rd of every month, rent is due on the 1st and late on the 11th. We prorate moving in, but do not prorate moving out, you go into a month and you buy the whole month. Notice of move out is due by the 20th of any month, otherwise you forfeit the deposit.

It seems like a huge hassle to be sending out billing, locking people out, adding late fees, taking move-out notices each and every day of the month. With the first of month system I know which exact dates every month things will happen. I can even plan vacations around specific dates if I need to and know that the other days will all be garden variety rental-only days.

If someone moves in before the 15th of the month we take the proration for the rest of that month and the deposit. If they move in after the 15th we take the rest of that month and the full following month (we don't want somebody to pay a 10 day proration and then move out, our policy is a 1 month minimum rental period), plus deposit. Most people are used to the 1st to 1st cycle anyway, with paydays, rents and mortgages, nobody has ever asked for the anniversary style.