I just wanted to get some extra details to make sure I'm relaying the information correctly.

@Jonathan Klemm thanks for the mention@Ali Farhat Jonathan is correct that you may still have some opportunity depending on the Zoning designation for the lot, and how many existing units are Legally Recognized by the City.You can Check the Zoning Designation here on the Chicago Zoning MapFrom there, you need to check the requirements for your lot based on the Chicago Zoning Ordinance (Note: RS-3 does not mean 3 Units.

Calgary market did not experience the crazy increase in price like Ontario, so the correction has been modest. 

In my experience, economic vacancy is typically more than 8%.Your NOI calculation is not correct.

I'm going to give my answer assuming the underwriting is correct and you've got quotes for your insurance and a few bids (and picked the highest number) for your renovations. 

Each option depends on your timeline, but a HELOC or cash-out refinance will likely offer the best long-term value, and it looks like you already qualify as REPS, which can save you 1000s in taxes if you plan your investment correctly.

I fell in love with the Lowcountry way of life, including good food, beautiful trees with Spanish moss, and stunning golden sunsets.

It may take several months of maneuvering to get them positioned correctly , but it will be worth the effort if you get them straightened out.  

@Dat Chung so to state the obvious, your somewhere around 0, correct?

I want to make sure Im prepared with the correct documentation to rent out my condo and would appreciate all opinions if im missing anything: - I have the rental application- I have my rental property agreement that I will have the renter sign and make copies of and provide them a copy.- I have the statement of condition that I will have the renter sign and make copies of and provide them a copy.- I will have them provide a copy of their tenants insurance for my records. - Will provide receipt for first and last months rent.- Im thinking of not charging security deposit because of all the strict MA laws and just using the last months rent as a sort of security deposit, thoughts?