There's a high chance that you are feeling FOMO from the returns in public markets, sell your houses for a loss, pile into stocks, and then see mediocre performance while real estate heads back higher again.I see this, and similar actions, play out over and over.Personally, I'd stick with the real estate rather than selling it.

Quick cash on a flip is going to 1. give you more cash to play with vs HELOC interest rates 2. give you an opportunity to 1031 exchange into your next investment. 

Check out this article that sheds light on how they come into play with this strategy.

Location plays a big factor into this question. 

However, from the stories I've heard it so far, sounds like it can lead me to the life I want for my future if I play my cards right.

Preference is cash-flow, but open to appreciation/equity plays as well.

Your number two is a bit different than what to expect on a short-term rental play.

Tenants will play games:1) Leave a minor home alone - no one should enter!

They are just playing with fire, really, but it happens everywhere.

A lot of new constructions are more of equity plays than cash flow plays.