After all my operating expenses and depreciation, I should have a lot of paper losses to deduct on my w2.

Sometimes your first loss is your best.  

You can still carry losses forward as well.

No income for 2016 tax year, loss calculated.If I don't get tax filed by cut off date, would Uncle Sam be penalising me for that?

Since FICO monitors how well you manage debt, completely paying every credit card down to $0 will actually results in a loss of points.

And since you don't believe our market and comp analysis, no loss there.

The Region Im looking to buy in is Northwest Arkansas.My questions are, is it feasible to turn a garage or barn into a single family apartment legally?

Part of your due diligence is gathering the trailing 12 profit and loss, rent rolls, property disclosures, etc. 

I am a loss mitigation specialist trained by HUD and can help clarify.

Unsure in your state, but the MLS's I am aware of are tightening restrictions on "assistants" using MLS...an unlicensed individual is not permitted the same liberties, like managing property, submitting offers, or showing properties...and violations may lead to loss of licensure...just be careful3.