Including financing strategies and cost of operating.

Material Participation in a Real Estate Trade or Business.This is pretty straightforward but you must materially participate in a real property trade or business, such as development, redevelopment, construction, reconstruction, acquisition, conversion, rental, operation, management, leasing, or brokerage.2.

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.  

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

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. 

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

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

Also, this creates misalignment of interests as the deal unfolds.3) Check the details of the operating agreement.  

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

I suggest reading this BP article on the core 4.https://www.biggerpockets.com/blog/core-four-real-estate-team