I have not contacted him yet, but Tal Tamir with Premier Cleveland Investmrnts, is a Cleveland native, RE broker and, investor who specializes in helping investors buy Cleveland area properties.

I still come across 1% deals in Columbus and Cleveland, with more cashflow and slightly cheaper deals in Cleveland, while significant economic drivers (OSU, Nationwide, Intel, Nationwide Children's Hospital, etc.) make Columbus a very attractive destination for appreciation. 

You can really make a deal work here in Cincinnati, Columbus, Cleveland, etc. 

I think you should look at other markets such as Detroit or Cleveland; cash flow is important 

As an investor and agent in Ohio, I recommend taking a look at cities like Columbus for higher appreciation or Cleveland for higher COC returns. 

Anyone have any experience in the Cleveland or Chicago market?

Abundance of multi-family homes in Cleveland and surrounding suburbs.

If your main goal is cash flow then you should definitely check out Cleveland.

Sporting events, medical care (a lot of good hospital, Cleveland Clinic, etc.), anything else? 

I invest, lend and am located in Ohio (about an hour south of Cleveland).