To support Michael Le's comment, building a strong TEAM is important.Real Estate agent, Lawyer, Mortgage Broker, Property Mgmt Company, CPA, etc.

We advertising in a rapidly gentrifying area with a lot of distressed homeowner.

There would be nothing worse than having 10 units and have to stop buying because none of them would support a pm.

I would think it would be a significant advantage in your advertising.

For specific properties I make a lender offering packet, here is the main page, I also include all the supporting docs at the bottom as well: 

I don't want to post it here as it may be construed as advertisement.

I'm not an insurance professional but I am a real estate investor/manager; which ever route you decide I would just highlight that you are getting insurance for a reason and it defeats the point to have 'coverage' that will not cover you when you most need it or go with a company that is not stable to support your claim should you ever have one - Me personally, I'd rather pay a bit more for absolute coverage that to pay cheaper premiums and one day turn for help from my company only to realize that they won't.... but the premium was cheap.

I jokingly was talking to a buddy about advertising as a section 8 rental (note - I co-own several Class C properties that currently have S8 tenants so I’m in no way disparaging), but it got me wondering.

I do have a day job that helps support any sudden expense I come across with the property.

I would make sure if you do send them any notices about this type of thing I would get supporting letters from the surrounding tenants that way it does not look like you are just targeting this resident.