There is risk with this approach that the tenant can have short residence or leave in Nov to January.  

Lots of people do short term rentals with pools, this is not very uncommon.

Two tenants leased the 2BD/1BA, and the studio ran on short-term rentals.

I’ll try to keep this as short as possible but I am at a cross road in life here and can’t seem to find the guidance I need. 

The appraisal district shortly thereafter corrected the tax allotment “anomaly” between the two lots, but the investor never made a tax payment and eventually lost the lot to a tax foreclosure.  

I have a couple of investments and am about to jump into a Short term rental while still being a w-2 employee.

As @Brett Synicky suggested, keep it simple, as a sole proprietorship.You are also not considering that you will have to pay $800 per year and per LLC to your greedy state.In short, get some professional advice instead of TikTok advice.

The question if such leverage is utilized can he weather any deflationary period?

My favorite source is Navy Federal for its long draw period of 20 years, and Figure for its fast funding.  

In general these are either growth markets or markets short housing that has significant hurdles to adding additional housing.