Why pay cash for keys when eviction are cheaper

Question

In Connecticut we have a law that sets a minimum amount for cash for keys at $2000. I most expensive eviction either marshal throwing them out was only $1,600

Samuel Eddinger · Answer

@James McGovern - it depends on how you define cheaper.  Evictions take 3 to 6 months.  Cash for keys is generally one month.  The amount you lose in lost rent makes cash for keys way cheaper (even if you have to pay more to the leaving tenant) since you are able to get the property back much sooner and rerent it.

Chris Seveney · Answer

Just going to tag along with what david said, its not about the cost but the risk and the time - if i can pay someone to move out and give them $2k and have all their content removed from the home - even if it was $500 to evict I am probably going to lose atleast 1-2 months (of time and rent) as well as have to pay someone to clean out the property. So on the surface it may seem cheaper to evict in most cases it is not.

That does not even take into consideration the risk of the judge granted additional time or court dates getting moved.

Caleb Brown · Answer

I think it's area and property specific. Some areas are cut and dry so there's not a need for cash for keys while others are a long process which is expensive(legal and holding costs). Evictions tend to have more damage then a cash for keys move out too(tenants get angry and trash the place or leave a lot of things).

Dan H. · Answer

Cash for keys rewards tenants for misbehavior encouraging this behavior and increasing the chance the tenant will do this to another LL.  What goes around comes around.

I never do cash for keys. I do not desire to reward tenants for poor behavior.

I have been asked about cash for keys.  I highly suspect the tenant has been rewarded for their misbehavior in the past.   I break that cycle.I explain the consequences of an eviction to the tenant. I explain they will have difficulty  Renting a quality unit, that I will ding their credit, that I will attempt to garnish their future income to recover what they owe.  They believe I will do what I state because I have always done what I told them I would do. My market has a low vacancy rate.  Poor tenants cannot obtain quality housing.  My tenant requirements includes no evictions, ever.  No excuses accepted.So far with a combination of good screening and good luck, I have never needed to evict a tenant.   When the time comes to evict our first tenant, I will hire the best lawyer and let the expert take care of it.  I will add the cost of the eviction to what tenant owes, and if the cost is not recovered I will consider it a cost of doing business. What I will not do is pay a bad tenant to leave so that another landlord gets stuck with having to deal with a bad tenant that I have rewarded for their poor behavior.  In addition, if I paid a tenant to $crew me, it may cause me to lose sleep.  Sleep is precious.   I would rather not pay the tenant, pay a lawyer, lose some rent but not lose one wink of sleep allowing the bad tenant to get money from me.Do not do cash for keys. You are encouraging tenant poor behavior.  The tenant is likely to repeat the poor behavior they have been rewarded for.Good luck

David Peschio · Answer

That’s a key point — while $2,000 might seem high for cash for keys, it can actually save you money in the long run. Even if your most expensive formal eviction was only $1,600, the real cost is in the time.

In Connecticut, the eviction process can easily take 3–6 months (or longer if the tenant contests), during which:

• You’re losing monthly rent — potentially $4,000–$8,000 or more.
• The tenant may stop maintaining the unit or cause damage.
• You’re likely paying legal fees, court costs, and potentially storage/removal fees after they leave.

You’re losing monthly rent — potentially $4,000–$8,000 or more.

The tenant may stop maintaining the unit or cause damage.

You’re likely paying legal fees, court costs, and potentially storage/removal fees after they leave.

So while cash for keys feels like a “bonus” to the tenant, it’s often the cheapest and fastest path to getting your unit back in rentable condition — especially in states with long and tenant-friendly eviction processes.

Wesley W. · Answer

I agree with @Dan H..  Even though the cash for keys might be a smarter business decision, you are reinforcing this kind of behavior within the tenant pool.  Not just for these individuals, but for all the others they brag to on social media about the bonus they got for not paying their rent.  As a whole, I think this hurts the industry as a whole.  I would not do it, on principle.  I understand I am in the minority.

On a side note, kinda funny that CT has legislation for a MINIMUM payoff to someone who has willfully breached a signed and executed legal contract.  Gotta love it.

Take your hard-earned money and invest it where it's treated better.

Kate Sanchez · Answer

@James McGovern  That’s a good observation. Aside from the cost, do you factor in potential delays or damages when deciding between cash for keys and eviction? Wondering if you’ve seen differences in tenant response or overall outcomes between the two approaches.

Scott Nachitilo · Answer

While evictions might seem cheaper upfront, "cash for keys" can actually save you time, stress, and hidden costs. Evictions often involve court delays, property damage, or tenant retaliation, whereas offering $2,000 (Connecticut’s minimum) ensures a faster, voluntary exit—avoiding legal headaches and vacancy losses. In New Haven’s competitive rental market, a smooth transition preserves your property’s condition and reputation.

Think of it as paying for peace of mind and a fresh start.

Samantha Wakaruk · Answer

Cash for keys is very situational on specific. Sometimes, the comfort of knowing the tenants aren't going to dump cat litter down your toilets or take a hammer to your walls is worth more than the monetary value. Sometimes it gets the tenants to make moves quicker when they have the short term gratification of money in their hands.

I currently have a seller that owns a triplex that is in the process of doing a cash for keys. Seller has a buyer but under the condition that the unit is empty and broom swept. The current tenant is a major hoarder.

We gave him 2 choices:

1. We go through the court process. 6-8 weeks turn around time when all is said and done. And there's an eviction on your record

2. We will give you your security deposit back in full if you vacate on this day. You can leave whatever you want to, but you need to be out by this date and time.

The tenant chose cash for keys. He got the bulk of his belongings out of the property and is currently in the process of moving.

Was it more expensive? Yes. Was it worth it to the owner so he can close this deal and move on? Also yes. It truly depends upon the tenant and the situation.

James McGovern · Answer

@David Peschio you can recover much of your court costs by pursuing Use and Occupancy under Connecticut state law

Why pay cash for keys when eviction are cheaper

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