Thank you all for participating in the discussion! I'm thankful for this community already.
@Brian G. - I like your perspective... Eagles fly with eagles!
@Jim K. A bit more went into quitting my job. To be fair to myself, I've been a HS teacher for 11 years and kept signing a contract year after year until I'd had enough unhappiness. With COVID uncertainties, I couldn't be happier about my decision. I am still working doing some gig-work in construction and also saving money by being a stay-at-home dad.
I currently own 1 SFH rental that was my first house I bought and self-manage the property. About $300 cash flow and will be paid off in 8 years. I have renovated our two homes while living in them and am familiar with that side of RE. I plan to GC my renovations or at least be very present often if I hire a contractor. I was planning on possibly going into the trades/construction field pre-Covid but everything is delayed so now I'm adapting and going all-in on REI. I'll do some of my own work but still hire out so it goes quicker, especially since I'm planning on starting with flips to build capital. I'm going into this knowing that the first one or more may be a "base hit" or even lose some. As Jim K said, I do tend to have the analysis paralysis in general, but when it comes to houses I love jumping in... that's why I'm mentally ready for this journey. Ready for those hard knocks. And of course, we will be as smart as possible so we don't "gobrokulate!"