@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.

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

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

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. 

I'm considering upping my aggressiveness on remediating this issue with something that will cover up the color of the mold so it will indicate better remediation efforts to future potential buyers. 

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.

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

In San Francisco, this choice is taken out of your hands and is instead a determination made from and by the Planning department.From an Investment POV, you are absolutely correct that combining the lower and the ground floor units is the best option to preserve your ability to perform a fast track condo conversion and generate the most equity in the shortest amount of time.

You are correct that you still have the original 50k as depreciation recapture.