Supplementing a tenant rent is illogical.

Those same colleagues worked past 65, many taking on menial jobs to supplement retirement.Then there was the bat house.

I see this as a supplemental niche strategy.

We have 11 units in #DFW and hoping to start to do Property Management for other investors in the area to help supplement our cashflow and scale our business. 

I wouldn't suggest any supplemental training/study material. 

I see myself slowly transitioning from full time rate race job in the next 5-10 years with real state supplementing other income.What are my next steps?

I suspect some of those landlords who aren't already listing with services like Homesuite, will move there as a way to supplement lost business.

Some grew up in real estate, some worked in construction which translated quite well to rehabbing, others came from a finance background and can feel comfortable working the numbers.I'd say hedge your bets and find a way to add/supplement what your currently doing with real estate.

Not having a job and supplemental income source or cash buffer torpedoes your pillar to negotiate.

Their is no reason to justify supplementing any tenants rent.Tell your tenant rent is rising to $550 in 60 days (assuming you are in a legal position to do so).