Given that it sounds like you already work hard and have a nice family (profile photo), I would suggest allocating any additional precious income-producing time to something where you have unique skills, a competitive advantage and can maximize your hourly pay rate. 

They have positioned themselves well with passive income producing property portfolios, have diversified their assets, and are happy as long as their own finances are covered.4.

Hi all,I'm a 29 y/o ecommerce entrepreneur and looking to get into real estate investing in order to turn my cash into income producing assets (and also have a place to live).

If this deal is only producing 200 to cover vacancy, repairs, and PM, Id run away.

Thus far this has produced great results, and I'm sure it will in the future.

The outstanding historical appreciation should continue to produce an outstanding ROI in subsequent years.Except for the house hacking aspect, this is what we do.  

Nothing fancy for either - just something to get our feet wet and produce some cash flow.My question is should we use money out of our HELOC to fund one or both down payments?

@Joe Splitrock is correct and my advice would be similar, stop consuming other people's content and start producing your own content.

Keep those costs down until you complete your education and start producing income. 

To clarify the deal is based solely off the income that the rental produces.