I want to automated this process for my business. 

If a STR has a typical homeowner's policy and just Aircover, and the property burns or a tree falls on the home, it will not be covered at all because it was operating as a business under a homeowner's policy.  

This is a business, like any other business.

I would bet that most title companies who get into the 1031 business don't know how to advise on or conduct much more than the simplest of exchanges. 

He owns his own business and writes off a significant amount.

Real Estate is a business just like any other and it's very hard.

If the average home price is $1M, and you want to get in the business of helping homeowners transact... getting a license seems like a way more obvious path to success than wholesaling. 

But as you journey through life building a family, starting a business and acquiring wealth it is ok to have a list of things that you should not have to do and it is ok to pay someone else to do it. 

I know that there are great oppurtunities in the area, but they won't be easy to find around here.

She told me to run the business; not my ego.