Thanks Hey Jeremy (great name reminds me of Vince Vaughn's character in Wedding Crashers)!

If you guys ever sell and move to an area she does not like, she will ALWAYS remind you about the mistake YOU made.

@Sam Ferguson Stick to the lease and send reminders in writing.

I can set reminders and what not to remind myself... but I was curious if anyone had utilized something like Excel to track their communications with people.

For example, your tenant's payment of $500 would be applied to the $50 late fee charge first, then $450 towards rent, leaving $50 in unpaid rent.The problem is that you never know if the court is going to back you because it's really a peanut-shuffling game.In your case, I would send the tenant a written notice reminding them of the policy and the outstanding balance.

I would ask them if they want to break the lease, but would remind them of the consequences in the lease for breaking it. 

., T2 Development, Chicago, IllinoisSteve, thanks for the reminder.  

Your significant other is very likely to remind you of this on an increasingly frequent basis. 

I needed this reminder!

Your post reminded me of a very similar situation my husband and I had with our first home we purchased together that I wanted to share in hopes to give you some perspective .