Massive job loss/bad economy. 

But you can't deduct losses.2.

Hey Guys,What steps would i need to take to find if it is feasible to knock a home down and build two houses? 

Title IV issuances, which are really only feasible for pooled investments like REITs or funds.  

It takes a lot of good deals to make up the loss of one really bad one.

For tax purposes the LLC's income or loss flows directly to you so whether you take the money out or leave it in the LLC you pay the tax personally.  

Based on what I'm reading, this should be feasible (but please let me know if this is not the case).I plan to start with a "house hack" - purchase a multi-family property with an FHA loan and live on the property for x amount of time.

If I were to buy a rental property that rents out for $500 less than expenses (mortgage, repairs etc) each month, will this loss lower the taxable income from my job? 

This is for sure a tax related question - but from what I understand about it is that because it is already tax deferred , that you cannot take deductions for losses from it.  

You usually have a feasibility period or due diligence period where all of these documents are disclosed.