What agency would make that determination?

But there are some challenges; notably it's easy to rehab out all your equity and it can be hard to find contractors/vendors sometimes.Also, a small town can be particularly vulnerable if it's reliant on one major company if that company leaves.

Companies like Proper Insurance can be both your homeowners policy and STR commercial policy in one. 

v=vdL7edltXIAAriz AG alleges that major prop management companies all used the same company for data

You should inform the title company that you'll be assigning the deal to an end buyer, so they postpone the municipal/lien search but proceed with the title search to ensure there are no issues with the title.

I work in tech, at a software company however have a real estate bug.

@Soumya Brijesh, I own a property management company in the Rio Grande Valley and can assist with any PM needs you might have. 

You are dealing with professional property management companies.

Why do these companies feel like they need to charge so much, especially upfront?

I suspect you can also hire a management company and rent it out as well.