Go into it with a positive attitude, not saying to expect it to fail, but definitely have some sort of agreement that will keep things clear if a break up does occur.

You are dealing with a group of people who are fundamentally stupid, and tripping them up is ridiculously easy.That kind of attitude is going to get you in a lot of trouble.

At this point, I would be more concerned that all security deposits (plus interest if required to be accrued and paid in your jurisdiction) were transferred to you - this should be easier to obtain post-close as it does not belong to the Vendor, but the tenants, and the landlord is holding it in trust.You do have the right attitude, chalking it up to education - sometimes the pricey lessons are remembered best.

I really like the M2M situation you have with PITA, and that is your best leverage...it's amazing what a for lease sign plastered on her front door will do to an attitude - unless she's better prepared than all of us think, SHE has no exit strategy to get into a new location. 

Her text message is filled with attitude, and assures me "you will get your money". 

I wouldn't call any of my tenants today dumb, but they don't always make the best decisions.My advice is change your attitude, change your management style or change your properties.

I've never understood such an attitude... what difference does it make, when it comes to landscaping, if one rents or is the owner?

You need to find out what the payment standard is for where your property is, and ask the housing authority to raise the rent to the payment standard.Here's the document that shows the payment standards for Chicago:http://www.thecha.org/assets/1/22/2016_payment_sta...I realize they may say "no," but if you go talk to them with the knowledge of the 2016 payment standards, and a nice but firm attitude that you need to get market rents or you'll have to leave the program - you'll have a better chance of getting it, I think.

There's such an entitlement attitude by people who are renters, who think that private landlords should be required to give them cheap housing wherever they want to live.  

Let the next landlord deal with that.I really don't understand the attitude that Rachel should take a chance on a risky applicant because this girl is in love or that she had good grades in undergrad land.