I currently have a 4/2 SFH/LTR/Section 8 house under contract and I am getting quotes for property insurance.

House Hacking is a good route to get started. 

Based on your current assumptions, you would be paying $1,229 per month out of pocket, leading to negative cash flow.If you’re house hacking and living in the property, it might still make sense because you're paying for housing anyway.

If you don't trust your agent enough to tell you not to buy a house, then get a new agent!

On the 15th year, the investor and I will discuss together whether we want to sell the house OR continue receiving cash flow.

View reportI'm looking to pitch this to an investor who wants to flip this house in Nashville, TN.

Pros: the cabin will be able to house our entire family, easy process to refinance.

If I was to trade a $300k house for a $310k house that will cost me $10k and $347/month what amount should I ask for to make up for these losses?

Parts of Garden City Beach are prone to flooding, so if you're buying a single-family house you'd definitely want Flood insurance. 

On the MGA side their in-house product is assigned to a different writing company depending on the state and risk.