In some cases, folks recognize losses that they can carry forward to offset future gains.

A real estate professional is allowed to take rental losses against ordinary income.

I suppose it could be a first time in history sort of thing but as far as statistics go the market has always recovered and always went up further than ever before.

With this being my first apartment deal I am more unsure about underwriting this type of deal and was hoping to get somebody who is more experience in multifamily to look at the proforma, T12 profit and loss, and rent roll to tell me if I'm missing something or to let me know of things that I should be looking out for.

They don't have a strategy for you because as I said, a one-off is a loss for a company.

Being a licensed agent obviously saves me the commission loss, but I would like to at least hold more than a year to stay away from short term capital gains taxes.

I’ve read enough to know that acquiring the LLC is a bad idea due to: unknown liabilities; tax liens and debts; loss of depreciation that has already been taken, and probably other reasons too.

(Sorry all the tax professionals that responded, I know you are better at this than your average consumer)Is there a way to ballpark how much bonus depreciation I may even be able to use as a tax loss to offset income?

After the dust settles, and that includes business overhead expenses, chances are you might even have a loss. 

Under this rule, if your average stay is seven days or less and you materially participate in managing the property, you can treat it as non-passive income and potentially use tax losses (like depreciation) to offset other income.