Once it is an investment property then you can sell it using a 1031 exchange which allows you to defer capital gains tax, and use that equity to buy new investment properties.

Law: Illinois has a law that requires (I believe) the insurance company to give a 'General and Special Taxes & Demolition Expenses' Form (Important info for this issue) to the city when claims/damages are over a certain dollar value.

Any deferred maintenance concerns?

Pm, property taxes, insurance.  

BUT you have less red tape, no tax returns, DTI, or employment checks are required.

There are conventional loans with 5% down as well which when your value increases or 60 months pass the mortgage insurance can be dropped.Student loans even if deferred are part of your debt to income ratio but the income from the rents on 1 or 2 extra units can offset.

I am researching a property that is scheduled for tax foreclosure sale in Wilmington, North Carolina, New Hanover county.The law firm that handles the foreclosure for the county says that the property will come with a “non-warranty commissioners deed” but the paralegal could not really explain what that meant.The law firm also says that they WILL sell me title insurance at the time of purchase.

Are they the same from a Tax perspective, Ordinary income versus long-term capital gain rates?

At this point they have no plans to resolve this issue other than increase taxes and replace wiring. 

Thank you in advance Deferred Sales Trust.