A majority of retail agents and brokers do have an understanding of the investment space, If an agent wants to focus on solely investment and wholesaling, what's the harm of working with a brokerage that specializes in that pathway of real estate? 

I would mention the fact that your neighbors are ok with your renovation and that the administrative nightmare is causing you and your family financial harm. 

If you want to lower your DTI there’s no harm in that, but don’t over-leverage yourself.

Every time I’ve treated these people with professionalism, honesty, fairness and never let it get personal to the point where they would want to bring me personal harm.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

He thinks the IRS would not fight this in court because they might lose a la the "substance over form" doctrine similar to how they got "crushed" recently in the Sumo-Holdings case.

I am a man of substance, of flesh and bone, fiber and liquids -- and I might even be said to possess a mind.

I'll definitely talk to my siblings because I would not want to harm them in any way or hurt our relationship.

With two children (my heirs) and multiple units, I am harmed by Prop 19. 

If one state comes out with some really harmful policies, you can hopefully weather the storm if your investments are spread out.