3) Should I just press to have a renter's policy instead, with the full year coverage? 

Normally once they have a good experiience they'll open up much larger amounts and will be pressing you for more opportunities!  

I am new to BP and have a pressing situation.My husband and I are interested in a property in the Bronzeville Chicago neighborhood and are teaming up with someone local to the area for this potential deal. 

You learn lot about "common sense" stock investing and 'high risk' in RE in general press.

It currently has a mortgage balance of 135k and property is worth roughly 175k.However, after meeting with him I KNOW he will be hard pressed to pay back this loan and I get the strong feeling he will refuse to leave voluntarily.

How do I, as a new agent, rise above the "bad press"?

Walk in elevator, ask someone close to the buttons to press 4, wait until the door opens so that I can get off the elevator. 

Landlord presses additional charges on the tenant .  

Personally, I would go after the couple for half the cost of removing the carpet and the smell and replacing with new carpet.If they really make 150k/yr, I'd be hard pressed to see them wanting to go in front of a judge and a bunch of strangers to argue that it was ok for their dogs to pee all over the house.The other thing I'd say is that it doesn't cost much to threaten them that you're going to take them to court if they don't pay for half the carpet.

Keep pressing forward, get creative, but whatever you do, DON'T GIVE UP!