What are the risks of not using a lawyer and relying on title insurance for protection for a deal of this type?

Don't know about NY but here in Texas the Consumer Protection Division of the Attorney General's office handles tenant complaints.

Secondly, if ensuring my contractors have WC doesn't protect me against having to pay for the contractor's injuries, how do I protect myself?

You may have overpaid for the property; you may be getting ripped by the PM; you may have rent set too low; or maybe everything is fine - no way to tell without posting up real numbers, which you probably don't want to do in a public forum.

He buys properties not through the public.

In response to Rondi's comment about a door in your home office-- I would consult IRS publication 587 for a definitional framework of "exclusive use" for your home office for conducting business.

Also, if you maintain an office open to the public, you could accept rent that way.

The feds are more concerned with their public image and advancing their careers then public welfare.

To protect himself from this, he needs an attorney's guidance. 

Does anyone have a good book they can recommend that focuses on asset protection for the real estate investor?