From there we identify properties that could have some potential and if you are interesting in diving deeper, 1) we do a thorough video walkthrough to give you a realistic look of the property, 2) we give a ballpark estimate of rehab costs (we do 40 a year with our GCs o we will get pretty close), 3) we talk through market rent with our property management team, ARV, and potential highest and best use.Ideally you find great investor agents who know their market really well and have a network of resources to provide you with enough confidence to take reasonable action. 

I would have to charge extra for the furniture to be here, knowing that people are going to put dings in it, spill stuff on it, etc.

---You won't know till you try. 

If that sounds like you, let me know if you'd be open to having a conversation!

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

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. 

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? 

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