the market is unforgiving right now with rates high, prices high, limited inventory, and tremendous demand for both retail and distressed properties.

I had a lot of luck with ASI ASI and Safeco early in my journey, and then I stumbled upon a different class of insurance companies that are more geared towards investment properties.My policies are currently underwritten by SES and they have been great to work with and very geared towards the investor.My insurance agent is a sage source of counsel on the subject and I bet he'd be a good resource for you if needed!

It's outside of the city limits and already zoned multi-use (previously used for a business and a home). 

After thinking about it further a good ol BRRRR at 300k is my best bet.

I think Airbnb is your best bet for cobbling together MTR pricing.  

Best bet is to try to work it out with the tenant.

Unless there is some other constraint, don't feel like you have to limit yourself to those two cities. 

Ian,With the limited of info known, the fees do seem slightly steep.

From there you can decide how to structure the LLC or limited partnership. 

Your mentor is right, but within limits.