I have been operating STRs for 5 years now, and there are many with much more experience, so you are sure to get other opinions.  

You will have higher premiums if the property is not operating within a formalized 503c nonprofit entity. 

Check with your local boots-on-the-ground team to learn about how that particular HOA operates.

Is it because people that operate and manage their own str can hit the 100 hour participation rule?

Including financing strategies and cost of operating.

By accelerating your depreciation schedules, you reduce your taxable income which in turn increases your operating cash flow.

I am semi retired at age 44, I sold my franchise business 1 year ago and have a very good idea of what it takes to operate a business successfully. 

We are not real estate licensed, so that would be the biggest area of opportunity to learn (we'd use a realtor at least in the beginning).We are considering selling the company because 1) my husband hates managing W2 employees/operations (but he loves working with subs) and 2) it would give us extra cash up front to reinvest.

You know, operate it like a business.  

Some loans like DSCR (Debt Service Coverage Ratio) loans are based on how the property operates as a rental (income, expenses, etc). 4.