No one has a crystal ball though so it is difficult to predict further than say 12 months or so (which still look strong).

We tell her to file with renters insurance, which is strongly encouraged by lease but not required.

That includes marketing, being at REI meetings, having an online presence, and there are so many other people digging for off market deals, so you have to find a way to separate yourself from the competition somehow 

so the market is pretty strong...so how is it that there are so many multi family buildings like that around what looks like to be good C+ and B areas but they stay on the market for months at the time...Is there something about Chicago laws ( other than the high taxes ) that i am missing and everyone knows about, so they dont "bite"? 

I do realize that many have made decent money at the very low end of the market, but that takes quite a strong stomach, and I believe also was a function of particular market conditions which aren't likely to exist again any time soon (IE these properties got absolutely crushed in the downturn of a decade ago and were picked up for a song.

Seriously, speaking though, I strongly recommend in speaking with a local Realtor.

Their economy isn't strong, unemployment is high, and drug use is prevalent.

We have two strong candidates right now and would love your thoughts on this.First, it is a higher-end rental ($2350/month for a small 3 BR, 2 BA single family home.)

Properties are priced quite low there and the presence of University of Georgia has created a high demand for students looking for housing.

Chapter 7 to completely wipe out everything or chapter 13 repayment plan which doesn't go away until dismissed for non-payment or the plan is completed over time and discharged.Check to see if current rent on the lease is at,above, or below market rents for similar properties.If personal guarantee and tenant has strong net worth then it could be a positive because if they default early you can go after them personally for the money.