There is something about relationship with other people I probably notquite understand.

 Or maybe not following the proper pattern in the right way. Or maybe unconsciously following a completely wrong one.

Tenants submit rent check that bounces back, apologize, convince me it'll never happen again,  once the check bounces back second time - say due to the payroll error they're out of disposable cash for the next 2-3 weeks. That is, until their  move out date :) And point at their security deposit I can keep for the last month rent.  Is it worth starting a scandal with them already?

Patiently refer the tenants to the lease agreement for the rent payment terms and late fees, explain that the security deposit can not be used towards rent.... And the tenant goes MIA and I receive no reply for another two weeks. Is it worth showing up at the condo without warning and starting a scandal now?

Since starting eviction process 2 weeks before move out is ridiculous, I focus on the condo showings.  Shortly after get an email form the tenant describing all sorts of problems in all areas of life she's been through recently and how (surprise!) they will not be able to come up with any  cash for me. But that they do absolutely need to stay in the condo for 1 more night past their lease end date. Tell them to go to hell? Prorate the rent for one more night to be deducted from the security deposit? In my turn, write a detailed email describing all the problems I have been through recently?

Agree to push back move out by 1 day and 1 hour, given the circumstances. The deal is that the tenants will clean out completely the condo prior to move out, and that we have a walk through together so there is a chance to point out at  any damages or missing items, and discuss or dispute them if needed.

Showing up for the walk through, I find the tenant there not quite ready. Fine. I agree with her to be back in 1/2 hour, walk back to the car, open my agenda, get on the phone... Come back in 35 minutes to realize no one opens the door to me. After a few minutes of waiting and knocking on the door louder, I open the door to find the condo empty. The tenants gone. The garage door key missing. The dishwasher not starting. A few items missing. And what's more fun - the condo in such a condition that would require cleaning services and disposal of personal items (I was surprised not to find any dead cockroaches in the fridge, and the small bathroom looked like there was a dog washed in the toilet bowl and then dried up in the dryer).

Still in the condo, leave a voice message to the tenant, follow with an email. Needless to say, I will not hear back neither the same day, nor the next day, not the day after...  I certainly am on the smart side requesting additional security deposit from tenants when I have a gut feeling I might need extra protection as the condo owner, - and it the extra security deposit cash just turned out to be useful... 

But there is something about the people relationship I am not seeing correctly. Or certain type of other people's intentions i do not have gut feeling for.