Personally I question whether the "extras" on policies like Proper's are worth the extra price. 

You need to make sure you're working with someone whose sending you personalized deal flow that actually meets your buying criteria.

I have been to a few of them personally its really something and the folks that own them are under the radar and make MILLIONS.

Perhaps there is a relevant book or podcast that you could suggest to expand my knowledge in this area.Considering you're experience with creative finance deals, which you mentioned previously, I am keen to hear about your personal insights and experiences.

And always check social media for red flags and I agree with Vince, always meet a person.  

You can’t use the property personally for more than 14 days or 10% of days rented, whichever is more. 

I'm going to exclude my personal residence from this because I don't view this as an investment, I need a place to live.Excluding my primary residence my current breakdown is 47% real estate 53% stocks/cash. 

The downside will have more to do with your business personality.

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

Personally, it’s something I always expect from a short-term rental, and it can have a huge impact on your reviews.To make things easier for both you and your guests, consider smart tools like locks, outdoor cameras, and smart thermostats.