The exception would be if this was already permitted for STR - short term rentals VRBO then it might be worth it based on location.If you just want to buy a home and have a unit to help cover the mortgage I would still insist on lower price point or NO HOA to help get the total mortgage down so that the other unit covers 50% of the overall payment.  

I would insist on it. 

For out-of-state STRs investors, is it normal for a cohost / property manager to insist on creating an OTA listing on their account to better streamline their systems?

The guests insist no one smokes but they did grill.

Good cash on cash returns take some work, like raising rent over time, doing light value adds, etc..If you jump in and insist on high cash on cash returns from day one you may find yourself in a tough neighborhood.  

And for a seasoned developer to insist on cutting out the GC would be a red flag. 

You claim they are bad landlords, but you insist on staying.

Always insist on three estimates for larger projects.To Your Success!

The seller was insistent on using probable future revenue rather than previous performance, which was a difference of hundreds of thousands.

Insist that your contractors store all tools etc out of sight.