@Ryan NunyaYou are correct that short-term rentals are a different animal for tax purposes than purely "rental" income as noted in the original post. 

From a purely financial return POV, cash is a smarter move than using debt on a lot of deals.  

I am saying it's a bad idea to invest in an STR purely for the benefit of cost seg to lower your tax bill.  

Yet, even Chicago has had its share of backlash from the PURE IDIOCY of thos so-called wanna-be 'financial experts' that advised & counseled equally foolish and future-vision incapable HUD staff members in Washington D.C. ofcs.  

Focusing purely on the numbers.Opportunity Cost of Renting: No AppreciationLet's start by understanding the concept of appreciation in the context of real estate.

Do you want it to be a pure "investment property" and not really looking to stay there?

My guess is there isn't going to be a clear answer based purely on math and analytics, so what makes the most sense for your current life and your future goals? 

It's a tax deduction pure and simple, not a tax credit.

I mean, it may cash flow 100$-200 per month of pure cashflow.

My goal is to spend 2-3 months a year there and rent it out for the remaining 9 - so I am not sure this initial property will be for pure investment purposes.