There's no reason you can't get a more accurate estimate to go off of.

I'm sure you could find someone much more qualified, however I have a very good friend that lives in philly that I'd love a reason to go visit.

So I'm house-hacking a 2-flat in Chicago and I'm trying to decide where to go from here.

Standard pre-sorted mail is the way to go! 

The property is in a distressed situation and would definitely need a remodel to sell for retail value (we might have to move some walls around to make the property more desirable). the property is around 60 years old with 995 sq. and around 400 sq unpermited on top of that and there is a mortgage of around 255k on it.

Thank you @Deanna McCormick I am going to go ahead and waive the application fee I don't want to do anything too drastic but I want to screen them and adjust the lease and rent rate and give them the option to renew or not once I make them aware of the expected changes and timeframes.

thanks @Joseph M. everything almost back to normal here.well from what i can tell the market has slowed down a bit, a lot of damaged property, i've seen 10-20k discounts in some desirable areas for SFR but that may not offset the damage

you have a higher coc with less money down seems the way to go.

My initial thought was that it is awesome you have a tenant who wants to go ahead and pay rent right out of their paycheck, as it would seem to me to be a huge plus.  

@Danny Farrell As others have suggested, the vinyl Allure-ish flooring is a great way to go.