"With a few exceptions, the first of which being "Dwelling units in owner-occupied buildings containing six units or less; provided, however, that the provisions of Section 5-12-160 shall apply to every rented dwelling unit in such buildings within the city of Chicago".If not in the Chicago RTLO, how are these properties governed?

That's understandable but being with the circumstance I'm currently in.

The folks that are buying while lacking in those areas succeed in spite of those shortcomings and are the exception."

With a short time frame, it is far too easy for stocks to lose value.As far as purchasing rentals with the proceeds, that would depend on how much you could safely leverage the funds and what kind of return you could expect.Long story short....there are too many variables involved to get sound advice in a short blog post.I would start by writing down a list of goals and then seek advice from a trusted tax advisor/financial planner and real estate professional to get solid advice, based on your individual circumstances. 

As far as the rehab goes I did a majority of the work except for hiring contractors to put in the new well and septic system.I still may consider selling so if you are interested I would be happy to show you the home.

I have had a few tenants pay late, and I always charge the late fee (except in 1 instance where they were robbed and had to replace check book). 

When there are two or more borrowers, but one or more will not occupy the property as his/her principal residence, the maximum mortgage is limited to 75% loan-to-value (LTV).Borrowers should take note of some exceptions to that 75% limit which are based on family-type relationships.Borrowers are eligible for maximum FHA loan financing for non-occupying borrower situations for FHA loan applicants who are related by blood, marriage, or law.

Best thing I have ever done in my life (except for marrying my wife and having 3 beautiful children:) I am now running a successful real estate brokerage expanding across the state.  

In particular, I'm curious to know if there's a particular set of circumstances or mitigation strategies that could make the increased risks (vacancy, credit, property crime/damage, etc.) worth it. 

@Brandon Hall I agree with you in most circumstances.