The communication aspect of RE investing will the most challenging for me since I have the hardest time getting out of my own way.  

Sometimes, having too much ambition can have a negative effect on many many aspects of your life.This partner of mine is already a business owner, and he made me aware that having too much ambition can lead to burnout, stress, and a feeling of failure when things are going your way.I suppose what I want people to take out of this post if they have not yet broken into the market and made their first deal is to not get overly ambitious.

I am not inclined to do business with PMs that are not leveraging the power of technology to gain efficiencies. 

@Akil Kariym-Bey, there are a few aspects of you plan that you need to think through:Buying a property below FMV from a family member.

The part time aspect is up to you.

The house hack aspect means it is a personal residence.

Such as the entire electrical platform had to be updated due to increased use of technology.

Doubt expenses would be as high as renting an actual house to people.I appreaciate you helping me with the cost aspect.

Any other FINANCIAL aspect that I am not thinking about?

I am a full-time technology consultant who got into real estate by what only could be God's plan!