Also, has the pandemic changed the way you are approaching any of these three aspects of your business?

Some people see the cash flow opportunity and don't fully understand that aspect of it.  

From this, you can gauge attitude which is important aspect of dealing with tenants.We do a chat casual interview on the phone before showing, mark down what was said, and one time caught the applicant in a lie when we got a different answer to the same question when she showed up to see the place.

I’ve come across a couple properties that fit my criteria in all aspects, except one.

I don't want to make money on a tragedy but I do want to protect the amount of capital that has been invested in this property + the liability insurance aspect so I can sleep at night.

I'd look at the return and long term aspects. 

A $300 inspection is for a professional to spend a few hours looking through each and every aspect of the home looking for problems.

The insurance was due to the commercial aspect.

You could enter into a partnership agreement in which you would have a document that outlines every aspect of the partnership like, funding, operations, responsibilities of each partner, disposition and so forth 

Keep a very close eye on every aspect of the deal.