@Jon Lafferty If your offering fair market rent and they are that much of an issue I would stick to my guns and find another tenant that can pay on time. If they have been there for several years, take great care of your place, never been late much and fell on hard times then it would be a thought to consider I suppose. From my 10+ yrs experience if you give them an inch they will take a mile!! If your calling every week now its a big red flag to me !!! If they get a discount now they will want more of one later somehow!!! Maybe they need to change jobs or do extra work somewhere, not your resposibility? Keeping a roof over your head should be #1 priority for them just as it is for you and the bank dont lower my payments so why should I lower rents? In a very special situation I could see lowering it $50 a month for a little while and then returning to the normal rate but even then if other tenants know you will do it they will want that treatment too. If your going to do that I would set ground rules for yourself and them and stick to my guns. Example- lived in the property 2+yrs, proof of job loss, only reduce rent for 6mo.
After having issues for several years trying to be nice and believe all the hard luck stories (which some might be true) I finally just said Ok here is how it is!!!!!!!!!! Rent is due on the 1st and no later than the 5th (4 day grace by law I must offer here) if you don't have the full amount of rent by the 10th including late fees you receive an eviction and its the same for everybody. This give the people that get a 2 week paycheck time to pay their rent if they have fell behind on the last check and came up short for the rent. I also use a 5 page 1 year lease b/c I feel its in my best interest in court for the protection of my property instead of a month to month.
The way I see it the faster I get the problem tenant out the faster I can find a good long term tenant that will pay and I wont have to call and beg for my rent. Been there too many times my friend.