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I have a tenant who is late on rent after having JUST signed an updated lease last month when we bought the property from the previous owner. He has a history of being late on rent. He paid 8 days late and the check bounced. He is now 17 days late and saying the late fees are too much and unfair. We have a meeting set with him tonight and my question is whether we should cut him slack, or make him pay up or leave. Fee details are in comment 1

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Sometimes investors lose money. Ask anyone on Wall Street.

Start the eviction process.

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With stocks, once it drops below a threshold, you sell to stop the bleeding if you know there’s little chance of it ever going back up. Get rid of this tenant now, it’s going to take a while anyway, might as well get the ball rolling now. Play hardball. The meeting should be to discuss the terms of his eviction, no compromises. If this sounds too harsh, then the landlord game might not be right for you.

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Instead of a late penalty give him a pay on time discount

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When you meet, ask for signed rent checks for the rest of the year. Then every month, ask them when they want it deposited and deposit it on that date. That’s what I do with my troubled tenant

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The last thing you want is to have a bad relationship and end up at court with a squatter

Due to the history of late payments, my SO wanted to make sure the fees for being late were scary in hopes that it would make the tenant stay on top of his rent. So... Rent is due on the 3rd, with a 10 day grace period. If the rent is still unpaid at the end of that 10 days, a $25/ day fee is accrued and it backdates to the day after rent was due. Also, the bounced check fee is $75.

Yes it's harsh, but the tenant signed the agreement

We allowed him to pick his due date when we wrote the new lease.

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Ask how often he gets paid at work. Have him make a payment every time he's paid. Is it biweekly? Then [monthly rent * (12/26)] is what this person should pay. Maybe whatever money this person gets burns a whole through their pocket, or like many others, there just isn't enough money to go around.

See if you can have him auto draft, or put their DD in your bank account. Which that part maybe is risky to have bank account info, but you could create an account thats ONLY use is receiving these payments, and then transfer them to your normal account after. Or maybe cash app or Venmo something could have a better way.

It isn't your job to micromanage him and his money. Evict and get a new tenant who will pay the bill.

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I’m sure it’s not just you. It sounds like the guy is not making enough to keep up with all his bills so he’s late paying all of them and trying to delay each one as much as possible

Treat it like a busines, not a hobby

pay and leave. considering the history of late payments and now him complaining about late fees being unfair or too much - time to go for this guy. Not sure how difficult it would be to evict him before his lease is up (assuming that he pays) but if you don't do it now you'll probably be dealing with it every month

And don't waive late fees, even the first time. It sets a precedent.

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