---You won't know till you try. 

If you know that something major will need replacement in the future, increase the monthly amount you are depositing into your reserve fund.

I TRIED to help you but you " know better". 

As a SFR investor for over 15 years I have been wrestling with this question in the past, because it feels like you should upgrade to "bigger".I know for sure that I would not enjoy the ownership experience that comes with a small 4F, because in Milwaukee that typically also means lower income tenants. 

So, when investing in areas they don’t really know, investors should research the different property Class submarkets.

i wouldn't tell you where you should move since i don't know you.also, a lender would be in the best position to advise whether you qualify for a specific loan. 

If this is something you are interested in, let me know and I will send you our projects. 

Quote from @Marlena Hawkins: Does anyone know what insurance (liability, E&O etc.) is required for Property Management companies in DC and Maryland? 

If you know any other investors or wholesalers please let me know.

That doesn't surprise me about NJ, knowing what I do as a person who's lived in the tri-state area for 25+ years, especially since becoming a father and coming to truly appreciate what NJ has to offer offer.