@Michelle SharkoAnswering questions in step by step fashion:- Is it a good thing to do or not is a personal finance decision and it depends on the person asking it, their risk tolerance which in part has to do with how this HELOC or line of credit works and how your personality fares relative to taking on new debt (a person more adverse to debt might have sufficient savings and temperament to pay down/back the debt versus a financially liberal person might get in over their skii's as).

I've run it through the BP rental calculator with conservative, medium and liberal scenarios and it looks like the property would cashflow between $450-$1,000 / mo. 

From what I read here on BP I think of OH as somewhat liberal and anti business or at least anti creative investor.

I google'd around for the USPAP standards after reading why he said it was a duplex, and sure enough it was a duplex according to USPAP standards, sorry agent, sorry seller, and sorry county of Alameda (he was super liberal with market rents on the 2 units that he had to call 1 unit, because it was one GIANT unit, so the rental income was actually fine). 3.

I doubt this will make it's way to jumbo (>$625k loans in our area) fixed rate competitive interest rate pricing loans, but I see high balance non-FTHB as likely.That's far from a certain thing either way, but generally when Fannie Mae's money will consider something, the value of that thing goes up because folks are more liberal with her money (a mortgaged offer to purchase) than with their own money (an all cash purchase).

For a business owner with $100,000 taxable annual income, the net tax savings for using an S Corporation instead of an LLC in taxes paid every year can be as high as $7,500.Holding PropertiesWhen holding properties as a cash flow investor, the LLC (or LP) is generally the better choice because an LLC has more liberal distribution rules.

I hold a bachelors degree in Liberal Arts and currently own the property that I live in.

Wasn't it so liberating???

Some of the "no money" conversations and strategies also depend how liberal you are (shades of @Jd Martin here) with defining your "own money".  

Even in Texas, a very Pro Landlord state, we have properties that are in very liberal jurisdictions and the judges delayed granting our evictions to give residents more time to pay their balance.