Not only would the rent cover your heloc costs (eventually) your property value increases giving you the equity you options for additional real estate investments down the road. 

Eventually I figured out that if I sunk all of my cash into properties, I wouldn't be able to buy any more for a long time and starting using some leverage.

If real estate with proper fundamentals is purchased well and appreciates, there are a few avenues to pursue:  LTCG tax treatment on an eventual sale;  deferring taxes through a 1031; or a refinance where there are no tax consequences.

but I think we will get there eventually too and we learned some new skillsets along the way.

He did eventually have success. 

So the property may break even or even "lose" $100-200 each month for the first year or so but that number includes the capital I'm putting aside each month for the eventual water heater, roof, or vacancy. 

When you eventually sell, your potential market is investors - this can mean many things, depending on the state of the market when you sell. 

I can't help feeling like he's been stockpiling funds to eventually file bankruptcy even while he swears he's trying to straighten everyone out.

I want to start a nonprofit eventually to help the poor in the USA & other countries, and I'm considering using my own money or receiving government funds instead of relying on donations from people unless they're just rich ****s.

Expanding my network is a priority, not only to find new opportunities but also to eventually be in a position to provide those opportunities to others.I know that scaling a business requires collaboration with others who can bring expertise in areas like financing strategies, legal structuring, and scaling operations.