I do have a fairly high percentage of my net worth (35%) in the PPR fund. 

I realize I don't have the actual NOI, but that price sounds super high for the gross income you're stating in your narrative.

If you are looking at FHA because of credit score, then I would work on credit scores to qualify for conventional financing or see if you can get a very strong coborrower with high scores.  

20% is not high for managing a STR.

Quote from @Vikas Jain: Yes, I have already seen the buy-in, im less concerned about that part of it, but just want to make sure its legitimate (plenty of opportunities where buyin is high but it doesn't always mean the product is good, just been burned in the past by others so trying to do better due diligence this time around)Their success rate, as of now, is 100 percent.

Zachary,Your concerns about Cleveland are valid—high property taxes and stagnant population growth are definitely challenges to consider.

I know a lot of Chicago investors are here too; but if you were in my spot would you recommend Chicago as prices are too high and I have never been to the city moving next year.

Rents are high and demand is high. 

If one has high living expenses, cash flow doesn't mean much and I definitely understand going for appreciation first.

I could come up with a down payment for an investment property in a different state easier than my home state at prices are pretty high in the 300-400 k just for townhomes.