I'm searching for an insurance professional to discuss the concept of negotiating group purchasing property insurance for a discount (similar to what is done through health care via employers).Are there regulations that would make this prohibitively difficult in the property insurance industry?

You also mentioned the real estate professional.

Im hoping the numbers work out. jijijijiji Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Then, I'd hire a full-time salesperson to be on the ground, who we'd ideally pay a commission to. 2.

These are reported and "retained" on IRS Form 8582.Of course, if you are unsure or would like additional guidance in determining what might fit your specific situation, please reach out to a CPA/Tax Professional who may be able to assist.

Let's break it down: Assess Your Financial Situation, Market Research, Evaluate Your Budget, Risk Management, Consult Professionals. 

On the other hand, I feel one of the main advantages of passive investments (via syndication/crowdfunding) is that I can hire a manager who has years more experience than I can ever hope to obtain myself.

Even though you may be hit with a hire tax rate if its your own business you can get expense the crap out of it and lower the taxable income as much as possible.

After you hire the VA, you have to train them.

I hired a company to complete the renovations and a public adjustor to help with my insurance claim.