A few years ago I stopped coaching, I sold my print marketing company (Yellow Letters) to care for my wife.

I definitely would pay attention to key macroeconomic stats such as population growth, job growth, and where companies are moving/developing.

It's an amazing market here with so much incoming growth due to population growth, job growth, and companies moving/developing here!

They must be very low odds because insurance companies are in the business of making money, not paying out maximums.

Do you have a property management company you use? 

I don't yet have an estimate on cost.I've never used insurance for something like this because A) I've never had an expensive repair and B) I fix most stuff myself on my Denver units.Question is: Should I file a claim or will the insurance company raise my rates so much that it makes it not worth it. 

Always keep record of where you told your insurance company that the property was being used for STR.

And the cost of legal defense , even if successful, will drive the company out of business.   

That style of learning and introduction to true industry catches my attention as having someone in the space that understands the space to bounce things off of and learn from seems to be the ideal way.I have through a handful of the webinars and follow up calls with different companies and they all basically pitch similar ideas and strategies.

If you plan to invest in multiple states or require advanced asset protection, consult a CPA or attorney to explore options like a holding company structure.