So my 12 year old is already looking for his next property, my 9 year old now thinks he want to do the same but doesn't yet have the comprehension of the basics to move forward, and my 14 year old just bought another pair of shoes!  

Foremost and Proper both offer up actual STR policies.Proper will be expensive but it is extremely comprehensive.

Thanks for such a comprehensive answer Alex.

Special Form coverage is always the most comprehensive, but comes with specific exclusions.

@Courtney Radmall we have proper for all of our STRs and while pricey, we feel it is comprehensive.

I am not sure where or how to start a pointed reply to this because it appears your fundamental "belief" of the market is radically different than the reality of it, so I have a thought that info may be "lost" until that foundational comprehension is first corrected. 

I would recommend The Land Geek over the others.In my opinion The Land Geek program is the most comprehensive, you can start with the toolkit to get the basics down then go to a bootcamp to really solidify the process.

Please help suggest markets (as well as will appreciate any investor friendly realtor + property management names - I realize there is the 'find an agent' feature on BP, but that doesn't seem to be comprehensive).

If you don't readily have full command and comprehension of every facet in this, absolutely get an attorney asap to do all of this, it is NOT an item to mess around with randomly found forms from the internet. 

I'm sure there is some type of comprehensive coverage out there.