I have a GC friend in PA trying to request 196k, as a “gap” to supplement whatever the HML cannot cover. 20% ROI, 6 months. 

My overall goal is to buy enough doors to supplement working full time so one day I can focus full-time on becoming an entrepreneur.

My husband and I are Teachers and Nurses but dream of supplementing our W2 jobs with passive/investment income. 

This ends up supplementing my income about $1,000/month give or take.

These do require more time and organization though.Looking forward, after 5+ years of owning a property, assuming you bought in an appreciating area, you should have enough equity built up via tenants paying down your mortgage for you and appreciation to refinance out of the VA loan (if you haven't already) or even cashout to buy more or to supplement your earnings.Theoretically, if you have enough properties you could refinance at least one a year.

The boss I was working for when  I read RDPD was a big factor in shifting my thinking from "supplement my retirement" to "get me the heck out of here!" 

This can provide a steady stream of income to supplement your W2 salary and build wealth over time. 

Maybe there's some semantic misunderstanding on one or both sides leading to all this confusion.I supplement my income with my public speaking.

We had PM teams that ran, on average, at 2x staffing for sec8, and FT maintenance staff supplemented with PT and outside vendors.  

If you really want to supplement your income, my thought would be to take out a HE loan (or some other 2nd position loan) and use that to fund a down payment on a property.