I have been leaning more towards the inland cities anyway simply because of the risk of damage factor.

A simple example is baseboards: if they're considered permanently attached to the wall like being glued on they're treated as a long life asset, it would damage the wall to remove it so it's like part of the wall; on the other hand if it's easily removable like being tacked or nailed onto the wall it qualifies for 5 year.

They also have a $1 million insurance policy that has paid me out for damaged items in the past.

Tenants either didn’t give proper notice to move , damages above the amount of the deposit , rents or portions of rents due, etc .

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How do you file a judgement against a tenant for damages beyond the security deposit?

Make sure you only add them to the liability section not the property damage section. 

As you can tell, this is a very big step for me and is quite nerve racking trying to make my first purchase as smooth as possible.

If the house attracts the type of tenant who is likely to skip out on rent or cause damages, it could be worth it.