I have an issue and need advice. I have a tenant who has been with me for 2 years and has been a great tenant. Today I received a text from my tenant stating, “she lost her job (contract ended) and that she won’t have Nov rent. Said she can be out by end out Oct.” This would be breaking the lease which ends May 2019. Do I collect keys end of October or work something out with her? How personal can I get asking about job prospects/interviews? I’d be more willing to work something out if I know there is a potential job lined up.

If she basically said she can't pay and it leaving, call it a blessing.

If you want to reach out and see if you can help through a temporary glitch, it can't hurt, just don't overextend your charity.

I say move on. It's just one tenant and they leaving you proactively, could be way worse. Find someone new and keep it moving.

@Cory Peters Usually under these circumstances we get presented with a problem-lost job-here you are presented with a problem and a solution. I would say take it; you can advertise the vacancy immediately, maybe at a higher rent.

What is there to “work out”? She doesn’t have a job and can’t afford the rent. Be happy she’s voluntarily turning over the keys and moving out without you having to evict her. Collect the keys and find a new tenant. It happens. 

I echo what others said...be thankful that she is voluntarily leaving and you don't have to go through the eviction process and deal with months of lost rent and legal fees. Let her go and start finding a new tenant. 

I'm working on my 2nd eviction in 3 months and believe me... it ain't fun! 

Ditto what they all said. Tell her as long as she is out at the agreed date and leaves it clean you won't file for eviction or in small claims for lost rent and potentially ruin her credit. Send her the required notice as soon as she is late just like you would any other tenant so the clock will start in case you do actually have to file. 

She did you a solid, breaking a lease isn't what people think it is. It's going to be more likely than not that a landlord has a duty to get the place rented as quickly as possible to reduce the burden on tenant. It's not like you can collect rent through the end of it and have a vacant unit. You also can't collect from someone who has nothing to collect against (typically that's: employment, credit/rent history).

You could leverage this by asking her to help you get it rented since you're helping her by getting out the lease... 

WIth that said, the risk in this is far greater than the reward... look at it like this:

Best Case: She gets a job, stays continues to pay rent through next contrat... maybe renewal.

Most Realistic: She takes reduced rent and hopes to get a new job, it may or may not work out but it's awkward for everyone trying to make up extra rent. Both you have to should the additional stress of trying to manage that...

Bad: She moves out, you have a month or two of vacancy... but key word is vacancy... ready for new tenant/showings.

Worst: She just stops paying rent, you have to go through eviction... she has nowhere to go and it just sucks for everyone. You're also not getting missed rent, can't show the place, and have to pay for eviction.

Work with her. Do an immediate walk through and see if anything needs to be fixed up/spruced up in order to list the place for rent November 1. Get everything in writing, and refer to the lease. I'm assuming  your lease states tenant is responsible if you are unable to get a new tenant. Again, everything in writing, and hopefully a smooth transition to a new tenant. Now, as far as the lease goes, if the new tenant moves in for November 1, I'd make lease expiring May 30, or a month easier to rent out place. Around here, winter time is bad to get new tenant. 

And, her damage deposit does not get returned until a couple weeks after new tenant moves in and everything is verified in working order and not damaged. No exceptions to this.