My motivation is being able to eventually be able to generate a passive income which would replace that from my job. 

The first house you sell will typically generate enough commission to offset that initial outlay of cash. 

Property is a 5 unit building and generates $480 per unit, $2400 monthly, $28800 annually.Annual taxes:  $2400Annual insurance:  $981Owner pays water/sewer/trash (I don't have those figures yet)Roof is new.  

I wanted to start a discussion to hear other arguments or inputs other than my self generate content on the following:1.) 

We generated one on accident for a client.

Generate your own numbers for your own proforma - based on your own market analysis and your own wisdom and experience. 

I also want them to have coverage because if something really bad happened, like a major injury or death to a tenant, I imagine that their family would start suing everybody (owners, manager, contractor, etc.) and would go hardest after those who they think are most capable of generating a payout, i.e. the insured parties. 

His son will receive a "stepped up" basis on the valuation and can either then take over the rental income from there or sell the properties using the value on the day of death as the basis, thus generating very little capital gain.  

You can offset that with more properties generating $100-200 cashflow but it seems cyclical.

I am not saying this negatively just stating that one never knows when ,what , and how things have come back to me clear out of the blue from these type of relationships . last point : I am on the backside of 60 70 years old is closing faster than I want it to , Many in my generation GET IT !!!