It is a duplex, built in 1900, with virtually NO updates since.

I havent looked at the zoning laws in your city but if you approach it by telling the city that you're basically just trying to update your garage, they will most likely be in favor of this because nicer properties make everyone's property values go up. 

Just do your regular screening on him. 2.

I currently rent, and dont have any real estate experience or training, but I have read a couple of books on it, and am a regular reader of the BP articles.

@Pandu Chimata ,The gain on the sale of the property is not taxed until your 2018 taxes are due in 2019, but if you made a significant profit, you might want to ensure that your W-2 withholding, if you have a regular job, is enough to cover the extra taxes you owe on the profit or make estimated payments so that you dont pay any penalties for underpayment of taxes you owe when you file your taxes 2019. 

Or do you just keep track of the new cost basis, thereby avoiding the recapture of that depreciation and convert it to regular capital gains?

I would be living under the same roof, different unit.Property numbers that I've thought about:Listed price: $79,0003 units (currently renting at $425, $450, landlord/$0) - month-to-monthRight across from school, in a Class C neighborhood, street on nicely kept residential with regular police presence, but sketchy loan places within 5 minutes and crime map is full of "disorders".House built mid-1800sMonthly ExpensesTax -- $138.75Insurance -- $62.50Utilities --$60.00 (split with girlfriend)HOA -- $0Vacancy -- $60.00 (5% of the time or unless I really mess up Valentine's Day)Repairs (cleaning) -- $100.00CapEx (replacements) -- $100.00Prop.

Everyone's posts helped but Im still trying to figure it out so here's an update to the situation.

Nevertheless, that's the way it is, which is why when you find successful women in this business they're usually super-successful, because they've done the regular work plus the dumb stuff that most men don't have to deal with. 3.

What will it cost for cap ex, management (when you grow and want this), regular maintenance, taxes and insurance (if not in mortgage) vacancy allowance, eviction costs, turn around costs to make the units rerentable.