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I am a relatively new landlord - 6 yrs.  When we first purchased our properties in 2005, one of the tenants had been living here for 12 yrs.   They have always been good tenants and have always paid their rent on time.   We have did had to raise their rent $150, $50 at a time over three years.  In August 2008 we had hurricane Gustav and everyone evacuated.   Since then they have been paying their rent late every month.  At first it was a week late and they said it was until they could get caught up.  That was two and a half years ago.  They always give me their rent check at the beginning of the month with a check for the late fee and a note asking me not to deposit it until a certain date.  That date kept getting later and later in the month.  That date is now at the end of the month which basically makes them a month late.   Sometimes I wait to deposit it until the 6th of the next month because I'm starting to get the next month's rent from everyone else.   My dilemma is - they have been here for 18 yrs., are quiet, keep to themselves., BUT, they also pay $200 less than everyone else and they pay late every month.  I only have six other units plus the one I live in.  They are my only original tenants since buying the property.  Do I put up with the late rent since they do pay the late fee (up front) because they seem to be such loyal tenants.?  Or do I get some else who will pay more and on time but might only stay for a year or so?  

Paying a month late is not acceptable, regardless of how long they've been there. I would sit down with them and have a very frank and open discussion about the fact that you like them, and you want them to stay, but if they're going to stay, they're going to have to pay the rent on time. If they'd like to stay, they'll have to agree to a payment plan to get caught up, and if that is not acceptable to them for whatever reason, they will have to vacate by X date.

I agree with Renee, have an up-front talk with them regarding their payments and why they are late.  

If they have been there for 18 years, and the apartment is still good (you owning it for 6 years or 1/3rd of their time) that's still an amazingly good tenant. You have to ask yourself a few difficult questions. 1) Do you want them to stay or do you want them to leave so you can raise the rent? 2) If you want the rent raised, can they afford it? 3) What is the quality of the other tenants, are they all good - just some don't stay as long? 4) Can you/Do you want to work with them to keep them there, just get paid on time. When you talk to them and determine maybe a little payment plan (and/or forgiveness) is all they need to get caught up to paying on time. In my contract, late fees can total $125 a month - waiving a few late fees and all may help them get caught up to where they are paying you back on time - it may also make it worse if you forgive those late fees and they still get worse and worse.

  Honestly, it sounds like they are trying hard to stay there and pay you what you're entitled - it doesn't seem like they are trying to withhold the money due to you. Talk to them, they should talk to you about what's happening. If you want the increased rent for the apartment, you may just have to be honest with them that it doesn't look like they can afford the place and try to get a good exit plan that benefits everyone so you will be able to increase the rent quicker and get people who can pay the increased rental amount.