As I am driving the internal cash register we all have just simply keep ringing cha-ching......not to mention the possibility of ruining the tenants stuff.   

But my real question is this, is there any "got-cha's" or strategy involved in the timing of the cashout refi AND moving the title from me to an LLC?

Hi Kenneth,Yes, but when renting--make "Business Decisions' about who will rent unit #2.What I mean is don't just accept someone because she is a "Hot Cha Cha" (you know what I mean).Keep your "Business Life" separate from your personal life--because it will most likely cause you business troubles if you don't.Pick you renters according to a predetermined plan (look in this forum for ways others do this) and vet them properly--they are going to have pay the mortgage with you.Also in a duplex the two sides must get along.If you sleep all day and apt #2 practices the tuba all day...Ouch.Just my 2 cents.

The HUD fair market rent definitely is lower vs CHA that runs the program in the city of chicago.

Hello BiggerPockets Community,I currenty have a 2 flat which I have a long term tenant who is paying cash living on the first floor & another CHA tenant who lives on the second unit above her.I wanted to go CHA because of the for sure money that will be coming in every month. 

. - I think you should definitely be calling CHA or whatever Chicago organization is providing the rental assistance.  

@David Cha The expenses for the WHOLE property will be entered on the Schedule E form, when filing your personal tax return.

If attorney state as soon as you talk to them or name them cha ching you owe in full even if you cancel.

@Mason Barnard here is some advice on C/D properties like this:Maintenance - estimate no less then 10% and this can be a variable depending on how CHA heavy the building is  Vacancy- you might be able to fill turnover quick but the turnover costs to get the property back into rent ready shape are typically twice as high.  

Regards,Billy Cha