We're going to do per-property math (as if each property were a separate business or self employed job, almost).

Another key factor is employment history.

Property management services are provided to the employing broker’s clients by persons licensed to the broker and with the knowledge and supervision of the designated or self-employed broker.Is the "residential leasing agent or manager" of the owner's property required to hold a real estate license?

I do work full-time, but this could conveniently become a weekend and night opportunity, my employer has very flexible work hours if needed..It is also worth mentioning that a long-term goal, besides investing, would be to open my own mortgage brokering or property management company.

Whatever area you choose make sure there is good employment, job growth and population growth nearby. 

Looking for a feedback from tax experts on the following scenario:A client is a self-employed (has an LLC taxed as S-corporation).

If this is a plan that you left behind from a prior employer then you can roll it over to a Self Directed IRA (SDIRA) account and invest in real estate.

That means it is fairly easy to collect court judgments from tenants who have a long work history at a major employer.

And this is all about being self employed not all can do that many folks can only succeed as a paid employee.

You can definitely benefit from having a retirement account that you are in total control.If you don't have any retirement accounts to rollover - then you will be limited to contributions of only $5,500 per year, so in this case you can probably have a conventional account (not self-directed) so that you can build enough funds before you self-direct.However, being a real estate agent makes you self-employed and therefore eligible for a self-directed Solo 401k, which is much more powerful then SD IRA.