Any damages  a tenant must pay for, unless its an act of nature or tree roots. 

Investing by nature implies there is a risk of loss like this.

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

He has stellar credit but is unable to make deals due to the sensitive financial company he works for and the amount of student loans he cosigned for his kids. 

As you have experienced this is the nature of these transactions.

Answer: No, buying an STR doesn't change the nature of historical passive losses on other LTRs you own and carried forward from prior tax years 

Sources for insurance and property taxes: Insurance - ValuePenguin, State Property Tax Rates - Rocket Mortgage.Low risk of natural disaster: Natural disasters can devastate your property and the surrounding community, leading to job losses and the closure of shops and businesses.

But humans are humans, human nature is what it is.

I, like most posters here, have a natural bias toward our area of investment/financial/business interest.  

Most fake this, but you are genuine.My response to you is then this.First, be careful, because human nature is a treacherous one.