My goal is to acquire cash flowing properties as a way to supplement my primary career in corporate finance (FP&A).

I agree with the gentleman that stated that they probably use the education piece to supplement what they cant get when market is slow and that you are basically helping them find deals.

Aside from my w2 job, I own a fairly successful mobile DJ business that I try to use to supplement my real estate aspirations.

Your friend has been lucky if no tenant has left in twelve years and skilled if roll over has not created any down time.Either way pricing rent below market is simply supplementing a tenants rent and has very little bearing on how long a tenant will stay.

It would be nice if I could get to the point where I could bring in 2k to 3k a month in passive income two supplements whatever I end up getting for Social Security when that time comes.

I think that's where local knowledge simply has to come in and you'll need to leverage people who actually  know the area to supplement the research you can do on your own.A data source I have used generally in my research is Data USA.Comparison of Brevard and Cullowhee - https://datausa.io/profile/geo/brevard-nc/?

Looking to get a multi family in my area and house hack my way to more properties to supplement my current job and hopefully learn more clever ways for REI as I go on.

Should be on market end of March then will continue to acquire multi-family properties.BP is a wealth of information and most importantly, a great place to network with like-minded people.  6 Units / 3 duplexes in N Austin TX areaGoal to get to 20 unit is 5 years (4.5 yrs now) - Not saying that is where I will stop, just a milestone.Why - to supplement income in retirement and to diversify portfolio. 

In other words, if someone wants to find only a handful of deals to supplement life goals, rather than go full tilt into RE investing, they can see how it fits THEIR plan.

Physical fitness will only supplement to it. may try cutting out one bad habit a week, and slowly work from there on.