You can also find good investment opportunities in your local area, and as many others have mentioned, your success may depend on the people you know.

Depending on the area, you may be able to cashflow more than the 300 per month.

Depending on the number of rooms, section 8 may also be a good option. 5BR is paying like 3K with utilities in PVD.Ultimately, I think you should sell it.

I've had broken windows, paint, and plumbing items flagged for repair but never stairs; although I have seen some really poorly constructed staircases and it's not terribly surprising to me that something like that could get flagged.Ultimately It's negotiable with the seller, although you should come to terms with the fact that you're an FHA buyer, and the seller would not have this issue with a conventional buyer; it entirely depends on your circumstances whether this is actually something the seller should pay for or not. 

You want to buy any new properties in a LLC but also depending on how much you want to scale your real estate biz, you may want to create a holding company LLC and a S-Corp if you get large enough.

I think this depends on the bank and of the allow helocs on rental properties at the time the loan was underwritten.

It all depends on what your goals are. 

@Ricardo T.It all depends on your risk tolerance and what gives you peace of mind.

Make an effort to gradually assemble a varied portfolio in order to optimize lifespan.

Depending on which part of Chicago you are located in, the MLS is really a powerful tool for leasing.