Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

If it is, I would do whatever I could to get good paying tenants in there right away,  If it is vacant, you are going to be running through cash like water through a sieve. 

I had a 104 unit complex and landlord was paying all the water.

The best way to own these lower price point homes is to pay cash if you can.

Pay the money for a piece of paper or go let my guy take on the project?

For rentals, staying with investments below $1,500 monthly rent is best because tenants who pay $1,500 and up generally do not remain tenants long term. 

Just keep in mind that less sought-after areas can come with slightly higher risks, but with the cash flow you’re generating, it can still be a good investment.

I wouldn't pay them anything upfront...I recommend you always pay for labor AFTER the work is done.

I have a long term rental and have a great tenant who pays on time and takes care of the place.

They always lacked something and I will never have peace of mind.