In all my deals I am bidding on now it is the number 1 concern.

The foreign currency exchange rate (FX) is always a concern whether you are selling and paying the tax or are selling and structuring a 1031 Exchange. 

Could you please explain the FHA loan and the benefits of it concerning starting invested with a small amount of capital (20k)?

@Harriet Baldwin When I told the tenant my only concern was the locks being changed, she demanded we call the previous landlord.  

@Janie VowlesAs far as I'm concerned they are not tenants until they sign the lease and give you money.

I'm also concerned because even if he is able to fix it up and rent it out, I don't want an accidental landlord with no experience choosing my next door neighbors for me, as you all can probably understand.

Has anyone had any experience that they can share concerning Real Property Management Suburban Chicago?

I would be concerned that he has other liens on the property, I would check with your foreclosures laws in the area, in Md. you could get in trouble dealing with someone with pending FC,I dont think he is in a great position to be negotiating.

I will admit though that I am 6'2 and quite the big guy, as well as usually carry some kind of weapon (I never leave home without a pocket knife and carry an asp if I'm concerned). you should be fine as long as you limit their access to your house to the garage, vet them over the phone, and have another person with you at the time of transaction.

So, I personally don't think you should be concerned investing in a cold climate.