If it doesn’t, buy it in your name personally and make sure you have plenty of umbrella coverage. 

Then I read the actual coverage and discovered the third company was providing twice the liability and up to a full year of lost rent income, which the first two companies didn't provide at all.

While I am not Batman, I can help Realestate Investors and Agents find Comprehensive PPO coverage that won't break the bank.  

So, if you have existing rentals they will look to calculate the debt service coverage.

It’s my first real property and only time will tell if it’s a successful investment or not but at least my understanding of risk was truly comprehensive due to artificial experience I got to obtain.

Have sufficient insurance coverage.  6.

Assuming "some bank worker" is the/a Buyer's lender, then John should not take direction and/or orders from the Buyer's lender.I agree with @NedCarey that if the title company does a search and concludes that Jim holds legal title alone and will give the Lender coverage under the Lender's Insurance Policy, then the Buyer's lender should not have a problem here.

@Nicho PruettDepending on the type of insurance the landlord has most coverages do covers liability, vandalism, fire, hail, windstorm, and malicious mischief.The landlord needs to speak with their insurance agent which I'm sure they have if the whole toilet drain system is ruined by the cement.

@Brandon Mix why don’t you ask a title agent to pull a comprehensive property list that includes property address, owner info, etc and then use excel to compare that list with the list of addresses from the City?

The only thing I'm not sure of is whether or not you're more open to lawsuits...I know there is umbrella coverage, but if a lawyer got wind that you owned a lot of properties free and clear, not sure if that could more easily make things bad for an investor.