Your dilemma boils down to two priorities: maximizing your investment growth versus creating financial stability for your personal residence.

But the only strategic thing about them is that you need to keep good records and hire a tax professional who knows how to maximize the tax savings from things you already paid for. 

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Regardless of which state you choose, be sure to maximize your liability on your renters policy and get an umbrella - this will protect you more than any LLC will. 

I had slept on the ground that night, me and my dog... over 1000 miles away from home pursuing the American dream.This was my second flip, I was out of my comfort zone.

I would study the different real estate investing techniques that you could comfortably afford to get into and find the one that interests you the most and go for it.

I spent my entire summer doing maintenance and ensuring comfortability.

I'd consider doing some kind of cash out refi on the property at a number you're both comfortable pulling out, while still leaving $ for reserves to maintain the STR you currently have.

That is the truth Nate, boy, I'd be exactly where I wanted to be, but I am definitely one that believes it's never to late, so I'm starting now to get ready for the next 20 years so I can retire comfortably.

For example, some areas SFH may exist but the clientele that move into them have to be comfortable with the neighborhood dynamic.