After various expenses (rent, food, gas, car payment, student loans, etc.)

This is in Carlsbad California, not too far from the beach and blocks from very popular shops and food.

Sometimes I go to the Food city at the intersection of 48th and Southern and the entire neighborhood changes drops to a C.

Will the contractor have to do other jobs simultaneously in order to keep food on his table? 

I would just make sure you write something up along the lines of "The leases states I am not liable and tenant should have renters insurance, but this one time I am offering X and if it happens again the tenant will have to use their renters insurance" If a tenant's fridge breaks, I compensate them for spoiled food. 

Thanks for the food for thought however!

He has had a mortgage on the property since at least 2003 based on city records.Anyway...the building is in a very good location with high traffic counts, numerous fast food chains sharing the same street along with a large retail strip with national tenants, an elementary/middle school and a small university (Indiana University-Kokomo, which is quickly  growing with a 125-bed apartment complex being built down the road and opening in early 2019) all less than a quarter mile away.The building has always interested me, and of course I have NO idea how much damage has been done to the roof and interior by both the tornado and the lack of use for multiple years.

Not recommending them per se, just giving you some food for thought to compare with the central valley back there in California.14 S 31ST AVE, Phoenix, AZ 85009 - $235,000"Four-plex with 100 % occupancy.

Indeed, as @Michael Baum mentioned, Punta Cana is one of the world's capitals of all inclusives and I don't know anybody who goes there and doesn't stay in an all-inclusive, which are probably less expensive than short-term rentals because flight and food are included.

)So Saturday came, I got the keys from the leasing office, and later that evening brought over food, a small roll up mattress, and some other small things.