Would be nice to see some precedence set for this to see playbook and potential legal pitfalls.

What are the potential pitfalls? 

It also helps when you have an experienced investor/ agent (your aunt) pointing out some of the pitfalls

I was wondering who might be brave enough to share any unexpected pitfalls/struggles that they encountered by being their own property manager of a multi unit apartment.As I began thinking about managing a multi-unit (especially one such as a 10-30 unit dwelling), I tried to think outside the box about possible unforeseen challenges outside of the typical calls "my sink doesn't work" or "my toilet doesn't flush". 

DSCR Has some pitfalls i wasn't aware of, I'm still halfway through the process so I'm sure I'll find out more.

What kind of grouping issues should we keep in mind to avoid potential pitfalls.5) What is a good process to maintain books for our real estate properties along with our regular business?

In order to avoid common pitfalls that can happen when buying wholesale properties, you need to have a proper exit strategy.

What are some of the pitfalls I do not see coming?

While there are certainly risks and pitfalls, if you're active on Bigger Pockets and asking questions when you need help you're going to be just fine.

I would love your input, maybe someone else can learn from my pitfall, haha.