Could be they'll do a forehead smack, apologize and agree with you.  

First of all, they already paid their debt to society and unless they have a big red F tattooed on their forehead, I'm not sure why landlords have an apprehension against them.

I’ll repeat something you might consider tattooing on your forehead: What we fear doing most is usually what we most need to do.

Yep, I'm aware it's a gamble (as a bead of sweat drips down my forehead) but I do have some reserves, I'm still doing a little consulting for my old company, and I have a very supportive gf (who btw is from Chicago).

If you're going to rent and want to get creative in the direction of selling you can:Rent to own >>>> Lease / PurchaseLease / with Option to PurchaseJust my opinion but.......Rent to Own -- Sorry, IMO, Loser here with a big L on the forehead.

You will be smacking your forehead about what the old you did-- and be much more confident moving forward.

Is there a counter on his forehead measuring the number of hits he gets?

As a newbie, some scammers out there see you as vulnerable "mark" with a $ in your forehead.

slap to my forehead!

(Slap to forehead).