The only real con is the fact that section 8 has very strict rules and regulations when it comes to inspections for renting to a section 8 tenant.

Wholesaling also has it own regulations coming down the pipeline... 

In a court situation, would email communication suffice for appropriate documentation for daily exchange?

Not just STRs.That's why if you've been through the trenches of defending yourself you wouldn't just mock the liability angles of protecting your investments beyond umbrella insurance, you'd know how to form entities and keep things separated appropriately.

A tenant complaining online might indicate that the property manager handled them appropriately, so be sure to ask the manager for their side of the story.7.

Are there any local policies or regulations that could affect real estate investments in these neighborhoods?

The only reason you should not enforce action is if its contrary to an applicable law or regulation...Here is another section from Seller Covenants:Seller agrees to honor requests for execution of endorsements of Mortgage Note from Seller to Buyer if made within thirty (30) days following the Transfer Date, after which Seller shall not be obligated to honor such requests.So if there was an issue with a prior document, after 30 days they can tell you to go pound sand - and based on court documents, this has happened. 

Cosmetic flips and short-term rentals can be profitable, but regulations and online marketing are essential.

First off, make sure you are communicating appropriately with the tenant.

I am trying to figure out that I have an appropriate insurance to cover the property.