The city does not have any duplex related permits.

There are many CPA's on this site that do so.In the meantime - feel free to ask any tax related question.

The widow is in poor health, and the son is focused on taking care of his mother. no current income/expense data.

If so, you and @George P. are buying the town up :-)  The fact that you've started at such a relatively young age means you'll have some pretty amazing life options a few years further down the road. 

From my research of comparable sales and a real estate agent relative in Italy it is currently valued at about 320-350k.

I'm relatively new to REI too.  

., a divorce decree), or The Borrower is a cosigner/guarantor on the related Mortgage debt and someone other than the Borrower has made payments on the debt associated with the property for the most recent 12 months, as documented with copies of canceled checks or a statement from the lender See Section 5401.2(b)(i) for requirements for excluding liabilities, including Mortgage debt, from the monthly debt payment-to-income ratio.Well - this is my third property that I am acquiring.

No expenses are deductible on personal days.In this case - The IRS may come and tax you on the rent and disallow you any expenses.On a side note - Allowing a relative to live rent free may require the filing of a gift-tax return if above the annual exclusion.

Garbage too is relatively flat.

Definitely start jumping into the community here and feel free to ask any questions related to Real Estate investing!