Does it get easier to deny people?

[Kelly N.]

We've always used a property management company for our other rental, but we recently purchased a second rental home close to ours and I thought we'd save some money by managing it ourselves. Now I know what I was paying them for! Our first applicant gave us a sob story and I made a rookie mistake by allowing her to view the property before doing an application screening. She assured me she had enough income for the rental, but it turns out she was counting child support that doesn't exist yet (she says she needs to get out of her current living arrangement before filing for divorce) and SNAP funds from an application that's in process. 

I know I wouldn't be doing her any favors by leasing to her when she can't afford it. Does it get easier to say no? Or should I just count on sleepless nights due to guilt over not being willing to give people a chance?

[Samuel Eddinger]

If your guilt is that strong on this one, hire a property manager!  When self managing, you have to think of it as a business.  Everyone has a story!  You should lookup "external locus of control".  Stated succinctly - Locus of control is the degree to which people believe that they, as opposed to external forces (beyond their influence), have control over the outcome of events in their lives.

So many people think that the world has failed them.  In reality, they have a victim mentality.  Move on from this person.