I'd insist that he find a non-related handyman or change PM's.I agree a huge red flag to me is 24 hours of labor.

Wanting to evict them are a tenant is late for a week or waiting months of non-payment to start the eviction process.

Even if you create a non-CA LLC, if you are managing the business from California, you will likely be deemed to be "doing business" in California and therefore likely subject to CA taxes.

A non-franchised Broker with six agents won't have professional training and resources, so a new agent won't be trained as well and will struggle to get started. 

However, non-government employers on average last less than 20 years.

So you would spend around $25-$30k a month (this was 15 years ago) on police details and require union gate and non union gate if you had non union workforce as well.In DC area, the utility providers are a huge challenge, whether getting permanent power, or water/sewer service etc - good luck.

HUD does not factor into the rent other amenities that might be included in the rent such as garage, basement, fieplace, central air, pool etc, that might command higher rent in the non-Section 8 market place. 

If borrowing, use a non-recourse loan since personal guarantees aren't allowed.

The other non-math issues I'm good handling myself. 

Hard money is a type of business loan for non-owner occupying investors.