Before my tenants re-signed a year lease earlier this year, they wanted to sign an even longer lease that would end in late October next year. But, that's such a bad time to find a new tenant when a year lease would have been perfectly timed to find a new tenant. 

So I rejected their offer and would accept a one year lease, which they signed. 

I thought that issue was settled until earlier this month the tenant blindsided me that they wanted to move and they had already found possible new tenants. They had already begun to advertise the place on Craigslist before informing me, and it seemed that they were ready to move out by by the end of this month according to the available move in date they posted on Craigslist. 

So, I assumed they had already found a new place already and signed a year lease so that it would end for them when they originally wanted to in late October next year.

I'm afraid that if I can't find any qualified tenant right now, then that place could easily sit empty through November and December.

I figured I'd win at small claims court, but it was an unknown variable how much rent I could claw back if it sat empty through November and December? Would a judge award me both months rent? Or, would I only get awarded one month's rent even if it sat vacant for two months and longer?

But, now, the tenants are telling me they won't be breaking the lease and moving out early on the condition that we sign a longer lease that ends next year in late October.  According to the tenants, they either need to break the lease now to sign a new one year lease somewhere else or get that longer lease that I didn't want because it'd be too difficult to move out when their year lease ended and find a new place that would agree to a six month lease.

I feel like I'm being more or less blackmailed by these tenants into agreeing to the lease they wanted all along but which I had already rejected earlier this year. When they asked to do this earlier this year, I knew I could find a new tenant at that time of the year and so I rejected it. But, by waiting till now to tell me they want to break the lease, my options are much more limited.

What would you do?

If I cave in to their demands, even though late October next year still isn't an ideal time to find a new tenant, it would still give me much more time to prepare and find a new tenant than what the tenants are threatening to do this year. And, I could avoid the drama of going to small claims court. There's also some road construction now nearby that limits the amount of drivers who might see the place for rent which won't be an issue by next year. 

But, if they can stay, then that means they haven't signed a new lease somewhere else. So, if I call their bluff, then they would need to find a new place and that will take them time to do that because I know they don't have a lot of free time to do that. And, if a landlord checks their references, there's no way I'm going to give them a positive recommendation. 

By the time they find a new place, maybe they don't move out till late November and it sits vacant only for December instead of both November and December. One of my biggest concerns with small claims court was how much rent I could claw back if it sat vacant for longer than one month. But, if it sits vacant only for a month and the judge award a month's rent, then its not as big of a hit vs the judge awarding a month's rent when it was vacant for two months.

My head says I should agree to their terms, but my heart...