It is currently operating as a long term rental, but the income would at least triple if we were to convert it to a short term rental. 

Once that amount is adjusted you'll have a loan payment updated based off of the rate and terms of the loan. 2) In you long-term expense estimates I don't see any assumptions for property management (7-10%), repairs/maintenance (7-10%), and vacancy (5%) so I would re-run your estimates based off of new expenses.

red states in general, FL, TX still have great deals and offer good benefits for landlords.

If the cost is more than the benefit, don't do the repair.

The property would rent long-term for $2,500 currently.

Often direct mortgage banks or lenders have an asset allocation monthly, quarterly or seasonally that they utilize to fund loans that are outside of 'the box' or need specific terms or conditions to qualify.

Both units are rented with long term renters and they bring in $2450 a month.

I own a couple short term rentals in broken bow Oklahoma and am working on acquiring more, and also working on getting into land development (goal of building smaller single family subdivisions).Looking forward to connecting!

Since a mid-term stay could technically last for 60 days, is that a Damage Protection coverage for reservations this long similar to AirCover?

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