Does the historical society in a certain town have a huge issue with ripping down old falling down red barns and fight people in court over it (Leaving the owner with an eyesore and a dangerous item on their property that costs them insurance carriers every year)? 

@Kieran DonahueI will also mention that your insurance carrier likely paid you at ACV value (value with depreciation applied).

This policy is your most broad coverage optionDefinitely look into these coverage's - personal injury, loss of rents (account for a full year's worth of rental income), water damage, a good amount of liability (at least 300k)For any investor I work with who has one property or more, I recommend an umbrella 100% to help further protect youI always recommend working with a broker versus a "big carrier" (st farm, allstate, usaa, farmers)Is your broker guiding your renewal process or are you dealing with carriers directly?

I know most carriers won't underwrite a policy on a property of this size & value based on its property value of 300k, but rather the much higher replacement cost which I'm guessing would come in at around 700-800k.

- switch to home possible freddie mac (beware of income limits)- bring more cash for larger down payment- use 5/1 ARM- permanent rate buy down strategies- negotiate your insurance carriers annual rate/premium- make sure you're using actual property taxes and not the lenders arbitrary rate that may or may not be higher than  your actual taxes- and othersIf you have any questions feel free to let me know.

I would say that the most important action to take in buying your first property (with or without an LLC) is purchasing insurance from a credible carrier such as Lloyds of London who specializes in investment properties, and structure the policy where liabilities are capped at $1 million.

Seem to be built better then Goodman and Carrier.

Any advice on carriers would also be much appreciated.

I just wrote one in CT that one of our carriers for $400,000 RC was $100 less than the next best rate which was based on $110,000 ACV for the same property.The second item that was confusing is what the payout will be.

Brokers won’t be able to do much everyone is at the mercy of the carriers.