Additionally since insurance costs are born by all policy holders is it fare to allow any person to qualify for insurance when the likely hood is that their home will be repeatedly damaged or destroyed in the future.

Also, title reps give you access to pull title reports on the properties and IMO a lot easier to compare comps.

Just to note, most title policies exclude such issues.

In my state, you can record the contract and it will show up whenever they pull up title.    

@Zachary Peacock If you go with a conventional loan on the cash out refinance be careful on how you take title on the front end when you purchase with hard money.

Also I was able to get homeowners insurance to cover the outside of my section of the building in case something happens. 

But I keep hearing people telling me not to rent out a property with a swimming pool because of insurance/liability issues.If I intend to insure it fully, am I still gonna run into problems?

He recommends to purchase more liability insurance."

Title or ownership in a entity, not individual.

You are paying them a monthly fee & insurance so they are more opt to consider you pay them to hang your license while learning the ropes.