I know that most people preach about cash for keys, I have had two tenants I have tried it on and it has always lead to an even bigger headache and elongated the stress.

I inherited one tenant when I bought a property that the seller moved in right before I closed. I knew the risk of them not paying as they hadn't even signed a lease but it was my first Seller Finance property so I was willing to take the risk.

They paid about 90% of their first months rent after my ownership (after a lot of follow up on my point) and never paid another cent. In Upstate NY it takes 3 - 4 months to get someone evicted and it's a stressful situation to begin with. I ended up trying to do the cash for keys, offered them a set amount, offered to forgive the rent they never paid and gave them 2 weeks to move out. They took it, and then dragged it out for another 3 months, kept promising they were moving out and found. place and yada yada but never ended up leaving. I of course (always recommend this) had my lawyer working on the eviction the entire time as I knew they were not trustworthy due to their lack of paying rent and lack of any remorse. So I didn't end up losing any more money than what was owed but it added about 2x the amount of stress with false hope and promises that never ended up happening. I did eventually get them evicted and thankfully they didnt trash my property (though they left a lot of trash that cost me $500 to get rid of but o well).

The other time this happened was a tenant I moved in who had a good job at a hospital, the hospital had a program where they paid the security deposit and first months rent. The tenant was responsible for the other 11 months of the lease rent and paid two months and then stopped. Following up with mass amounts of excuse and ghosting so I ended up starting the eviction process per usual. I offered the same terms as the previous one and they were very happy with it and made the usual promises. Move out time came and they hadn't even started looking for a place etc etc. 2 weeks out from the court date for the eviction they upped and moved and didn't even request the funds (not that I would have given it to them anyways because they were 2 months past the agreed upon move out date). Thankfully the tenant above let us know that they saw them packing a haul so we went in, all was good and non damaged and empty. Spoke to our lawyer, posted the necessary documents to confirm it was abandoned property and went on to have it cleaned and a Section 8 tenant moved in.

My question is, I hear everyone talk about cash for keys, cash for keys, cash for keys. But so far I have found it to be an emotionally exhaustive process and have had zero luck. I have only tried it twice so just wondering what the more experienced investors think of this, or is this just something that people talk about to try and make a real estate investing negative seem not so bad?

REMINDER: Even when you make a deal with a non paying tenant to always continue the legal process in tandem. Never trust that someone who doesn't keep a promise on paying their lease contract will also keep their word on leaving. It's a game and they have probably won it in the past.

Jamie O'Connell

Upstate New York, New York

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