It's not so much - how can I make money and survive on this - it's more about - how can I have a bunch of land to play and relax on and have it partially pay for itself.

I can't imagine the muscle power required to get that level of deep scratches.  

An empty unit equates to an 8+% drop in yearly rent for each month empty, wouldn't it be better to drop the rent and relax your standards a bit, rather then leaving a unit empty for too long?

Determine what premiums you will charge a tenant for such an animal in terms of additional monthly rent, security deposit, lease commitment, as well as renters insurance as my friend @Derek W mentions.I've made way more money by solving others' problems than by getting into arguments about why someone's (arsonist) kid is really just misguided or that their dog is normally a sweetheart (as I apply tourniquet pressure to my bleeding calf muscle with fang marks).I'm still trying to make Cesar Millan's 'shsshtt' technique work on my unruly probate clients!

After a long day of work: to unplug another's toilet, to reset switches on the electrical panel, to call the roofer to inquire about checking leak - none of these are in any way relaxing.  

Relax and update your lease for the next go round.  

You are already where you are and looking at making it better so just relax so you can do step 2 2) FOCUS.....your thought process is like a bowl of spaghetti (mmm, makes me hungry) mixed with frustration.

Relax.  

Eccentrics who made their million and just come to Kauai to relax and get away.Everyone is pretty laid back and unassuming here, but your neighbor or person hanging out on the beach could be in the next Movie, Free Music festival, or own a billion dollar company that we frequently use the services or products of. 

If the home state has tight restrictions then they gravitate here to vacation where its much more relaxed.