It currently cash flows $700/month after taxes, HOA, insurance, etc.If I sold, taking into account the costs to sell, I could make between $390-$440k in profit. 

LL commits to rent unit for certain amount of time and government determines tenant can stay as long as they desire.  

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

Hi Jason,Here's a few things I'd be mindful of:Separate Personal and Business Finances - get an EIN, open business bank account and use it exclusively for businessMaintain Documentation - keep records of all business transactions and contractsComply with Legal Formalities and Tax Regulation - adhere to all state specific regulationsIn terms of the STR and LTR, it's generally recommended to put them under an LLC by transferring ownership or quitclaiming.

- Do you have a current need for that cash flow generated from the tax savings? 

There is a number of threads about it in the tax forum. 

Getting the COC% to meet that pref has become increasingly difficult with interest rates, rising insurance and taxes.

My accountant asks me to talk to them BEFORE I make major money decisions so that they can help me protect myself from taxes.

Wouldn't this property now qualify for the 1031 program and defer your income taxes?

You can sell both units to one buyer, but that buyer now has two properties, with separate tax bills, etc.