Tenant expected keys without rent upfront

[Jack B.]

I collected a hefty holding deposit from them a month ago to hold the place for them. Last night was our appointment to meet and collect first/last months rent, get the lease signed, and give them keys. Got it all done and I brought up twice that all that's left is payment (5K) and I'll be out of your hair.

Then started the hemming and hawing, oh, well I have a few checks going through, etc. I collected the keys off the table and told him as a matter of policy I treat everyone the same (he owns a construction business but had a bankruptcy and lost the MANSION of a house he was living in after the economy tanked and he filed bankruptcy) and don't exchange keys without first/last months rent.  He was embarrassed a little but understood. Offered to meet up with me coming to my house the next day (I visit tenants at their existing place of residence before renting to them). 

What miffs me is that he was well aware per his receipt for the holding deposit and our back and forth texts and emails that payment was due before exchange of keys and I drove out there late at night to meet up with him. I didn't get back home until almost 11 PM. Yet he didn't have the money so it was a wasted trip. Tenants...