The 2008 timeframe was different and in situations a lot harder than now, but this market will shape a lot of investors that found their new market, product to focus on, and/or to dive in deeper when times get tough.   

I have a HELOC on my Texas primary residence and am considering a house hack for my next purchase.

So, when investing in areas they don’t really know, investors should research the different property Class submarkets.

In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

REAL Estate in any form takes capital.. don't let anyone tell you different 

Each Prop mgr will be different but yes, mine would handle all of those things that you would need.

Don’t forget heloc, DSCR, 2nd on primary, borrow from retirement accounts, credit card cash advance, property reserves, home improvement store credit, etc etc.

Your first property should be your primary residence, period. 

How would the situation differ with a home that’s never been a STR but would become one, or a home that’s for sale now that is a current STR.

I have my own thoughts on what the differences are, but I am biased so I'm curious -- as a listener to both shows what do you think differentiates the two (or should differentiate the two?).