If he has no assets at time of going in, will they come back and take assets from you?

Personal financial statement.  

Great assets (cashflow and appreciation, low to no cap ex), steady (low cash flow, good tenants, slow appreciation, low to no cape ex, and dawgs (low to negative cash flow, lots of cap ex coming, aggravating tenants).

Would it be helpful to you as a landlord have have not only the day to day automated but also have guidelines and quick access to local regulations (where there is constant change) in your assets markets to help you stay compliant and avoid potential lawsuits/fines?  

@Elani SevillaTo finance real estate without a W2 job, focus on strong financials and business income stability.

I want to invest in real estate to heavily supplement W2 to open up options and financial security. 

There is no "magic number" of properties to own, everyone has different goals and financial situations to get to their personal "magic number".  

My advice: focus on building a strong financial foundation first save consistently, manage your credit, and educate yourself on real estate fundamentals.

I'm a financial planner who works with real estate investors - we have a client who plans to renovate a Clinton Hill (Brooklyn) property that has been in his family for generations into a multifamily rental.

However, understanding all the costs of buying a real estate investment property will help you avoid costly mistakes.Buying a rental property, holiday home, or property to flip can yield short-term and long-term financial gains.