Finally, short-term rentals can offer potential tax advantages, as many expenses associated with the property may be deductible.

When you say "we," are you speaking about your business or your personal tax returns, or does your business flow into your personal returns because you file as a sole proprietor?  

My ultimate goal is not using my savings during this process, because I want to train myself from the onset to think creatively and not deplete my reserves instead of finding a better deal or more productive relationship.

Utilized a low down payment loan, maxed seller credit, tax proration and closed on the 1st of the month to maximize my cash and acquire this property What was the outcome?

If you feel bad and want to save people money, start with a free pre-screening.

Will the property taxes skyrocket?

You need to have the income and tax liability to support the depreciation.

When you add that: "The downpayment and closing costs would be one large hurdle"; I can't tell if you can only afford to do this once (thus tying up whatever you have saved) or multiple times.  

Could help you save some serious $$ if buying and selling there and can also get you access to their MLS systems.

They are mocking these up with interest only loans and factoring back in the tax deduction as if you qualified for the tax benefits of a real estate professional and factoring in the diminished first year property tax (since its not a full year).