CHA (Chicago housing Authority) is tough in itself to do business with. 

In addition to low inventory, something else is at play here in this market, and across the country.Many people, my self include, believe we may be at the start of an increasing inflationary period in the US. 

The plan would be to have 2 separate purchase contracts with closing of the 2nd property to occur after closing the owner-occuped FHA loan. 2) I'm now trying to evaluate a commercial loan for the 2nd (or both properties), but not sure how that could play out yet.

I have never played the "guess what this is" game with tenants.

I would start with the rich dad poor dad series which gets you in the right mindset and has different authors as you go along that are masters in their fields. 

If you do a smaller 5%, maybe even 3.5% down payment, it is much easier to get into financially, but then you're just playing catch up longer in terms of monthly payments as opposed to doing a larger down payment.

Then He plays very loud music, won’t let anyone in his unit including the water department cause our water bill and electric bills have skyrocketed, when the contractor goes upstairs to fix the upstairs unit he lets everyone know there was a suicide in the unit which we feel will scare away another tenant when we are trying to get it filled.

(Yes Sir Appreciation play) My next second (vacation home) will be a cash flow play, already have the property lined up.  850K with 8.6K in monthly rentals

Makes me wonder how and if SEC plays into this situation.  

@Joe SplitrockBest post of the week, I remember sitting in the computer room in small town Oregon at my school playing that not realizing the rest of the country was getting dysentery as well.