I think the situation was different in the mid 90's when you could rent a place in Park Merced with section 8.With regard to quality of tenants and I can only speak for the russian-speaking immigrants I know who have section 8 -- they tent to be older, retired or semi-retired and will probably skip a meal first rather than be late on rent :)

This may add $200 a year to your insurance but I assure you after 25 years doing corporate housing never skip on the insurance. 

If you provide free housing, then I guess skip income verification.

By including all of them on they same lease, they all will be responsible for the full rent payment.If one or two skips out, you can hold the remaining tenant accountable for the full payment.

-Who should I lean on- do I work with my agent or skip it and just get a real estate attorney?

This home built in 1950 had floor joists that skipped the planer that we take for granted today.  

So would just sticking with a good umbrella policy and skip the LLC still be a wise choice?  

Send the leads to a skip tracer and then call the leads instead.

If it is only marginally positive, a lot of people skip it as not worth their effort.

Imagine you came over for breakfast and told me you only like grape juice.