Some of the best performing properties can have an occupancy around 60% for the year and sometimes lower.

In my experience, the local banks are going to get you better rates and lower fees with their commercial loan products than the "DSCR lenders".

The worst they can say is no and give you a counter, or they ignore you and you try again a little higher, or wait a few weeks and try a little lower.

It's effective interest is similar to Mezz-debt at current rates but a bit lower.   

You really don't need that LLC until you pay off the property and it's questionable if you need it then as long as you maintain your property and have correct insurance.Yes to wind insurance, not sure about hurricane.I use Foremost STR policy for one property.I am about to switch to USAA (retired Navy) for another because they quoted a policy that was 3k lower than what we have.

I recommend using a lender that non-reporting to personal credit and can close under the LLC to keep your DTI lower and overall your personal liability profile more bankable.

Negotiation LeverageThe long market time gives you leverage—consider making a lower offer with seller financing.Point out the high rehab costs to justify better terms.Offer flexibility (quick closing, interest on seller financing) to make it attractive to the seller.Final ThoughtsYour best bet might be to negotiate seller financing for acquisition and use a rehab loan or private lender for renovations.

While you likely won’t owe taxes due to the loss, filing is still required since the rental property is located in Missouri.Kansas (KS): As a Kansas resident, report the rental loss on your KS state return (KS-40) since Kansas taxes your worldwide income, including out-of-state rental activity.Tax Impact: The rental loss reduces your federal taxable income and may lower your overall state tax liability.

If the numbers make sense, the plan is to approach the seller and attempt to get a lower price for this "2-story" building which has vacancies, since that's what the owner is selling.

House hacking could work if you find the right deal, but I’d also look into BRRRR or flips in secondary Florida markets like Tampa or Jacksonville, where acquisition costs are lower.