I have flipped two houses with my wife, and I have read virtually every book on the Bigger Pockets bookstore (see attached image).

For interior alterations, The City's website states that I can submit a RAAC Document (attached), Residential Automatic Approval Certificate, acknowledging that no plan review will be conducted since the drawings will bear my stamp and signature.

Thank you for the input, I will measure the distance from the window sill to the third floor carpet, it's pretty low, let me see if I can attach pictures.

Whatver you decide, you'll want to ensure the proper addendum is attached to the lease to specifically outline how utilities are handled and charged if charging tenants. 

See attached Invoice.Through this letter, I hereby request proof that I am indeed the party you are asking to pay this alleged debt, and for proof that there is a binding contractual obligation to pay this alleged debt.

In order to sell or refinance the home, you will have to pay off the amount owed to the program.People are led to believe they can write off the cost of your payments [principal + interest] on your taxes because they attach the debt to the property tax collected on your home.

What happens if during an upset sale you win the property with a bid of $100,000 and it has a $300,000 mortgage attached.  

I copied this from the Chicago RTLO which is attached to the CAR lease:-Before a landlord can deduct expenses for damages from the security deposit, the landlord must provide the tenant with an itemized statement of the damages within 30 days of the date the tenant vacates the dwelling unit.

The first month was an intro letter and every month after that will be a Market Brief, which I've attached here.

A may be wrong but I don't see how you can get a clear title on either of the properties with mortgages attached.