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.

It wasn't the restaurant aspect, it was my property that I wasn't able to refinance with ANYONEit's currently a portfolio loan with local credit union.

That is what we did with my primary house this summer (minus the multi-family aspect).