Plus, if you decide to do one of the other strategies in the future (such as BRRR'ing or out of state investing), you'll be much more prepared to do it if you have a few HH's under your belt--a ton of the lessons you'll learn from a HH can be used to succeed in other areas of real estate ...in fact, I'd say that a HH should be a necessary prerequisite to the more advanced strategies (like flipping) for most folks!

We have one fix-and-flip under our belt, and are currently rehabbing the house we’re living in as well as adding an ADU (we don’t plan to sell this house). 

If I can get 4 or 5 TK properties under my belt I could likely leverage a few of them to afford some larger RE purchases when I am ready.

Suddenly, buying your permanent house with one rental under your belt becomes plausible because you have a job, some rental income, and you might have thousands of dollars of equity from that first property. 

@Blake Clifton, I would opt for 3 units personally, but I also have several remodels under my belt and actively look for value add properties for the discount in purchase price.

They're either gurus who don't actually wholesale deals (which is almost all of them) or they're people who only have a couple of deals under their belt and feel like after a few deals they know everything.

Assuming I had a property under my belt and I was looking for work, would that improve my chances of getting connected to GCs? 

You need to learn the market ( where and what price to pay ) 1st , get a few under your belt .

I had a blower motor go out in one of my properties back in October which was $900 to replace.

But once you get some education and networking under your belt, it'll be easier.