@JT Johansen sorry this got a little long, I think there's some helpful stuff?
My journey is as such, I have an S-corp, mainly for tax purposes, I am a freelance television editor and one day my CPA recommended the infamous Rich Dad Poor Dad book. He talked to me about how real estate investing is a great approach to retirement income. After reading the book I was hooked. The next thing that happened for me was just general discussions with friends and family about investing in real estate. And honestly looking back what I thought was a good idea was not.
One day a friend of mine told me to check out the Bigger Pockets podcast, fyi this is true and I have no affiliation to BP. I listened to one episode and immediately wanted more. I don't remember how many episodes there were when I started but I think it was around 187. I listened to ALL of them. Even if it didn't pertain to what I thought I wanted to do. Eventually I started to understand topics and know what certain real estate jargon meant. I love to learn new things so I would always check out the books mentioned at the end of the podcasts. I definitely didn't read them all, not even close, but picked up a bunch that either seemed to be repeated mentions or ones I thought would help me create my strategy.
After reading a few, and I'm still reading them, I started to come up with my criteria for where to buy. I crossed referenced a lot of random things because I'm no expert but it was fun doing the research and coming up with my own vision of where/what the future could be. I looked at things like "hottest real estate markets" (past and present), cross referenced with job growth, population rates and where "the cool" kids were moving. Trying to understand what industries were thriving and where they were going. For some reason I felt that google fiber was a nice perk for an area, I mean everyday more and more things go digital and google fiber is lightening fast. I investigated local industries, read business journals and scoured BP for topics in my top 5 potential markets.
My list eventually narrowed to a handful of markets at which point I started to try and make connections and find out who I knew where or who I could meet and talk with in these areas. At this point I was dealt a dose of luck because of the connections I had in KC. As I mentioned my mentors in KC were willing to help me along the way (and still do) and were always giving me advice, but also very encouraging when they told me that everyone does it different and that I will make mistakes.
Eventually I started running numbers using the BP calculators, I knew what my investing budget was, and started making offers.
I really think a key to investing out of state is going to the area. I was born and raised in CA (just North of you actually) and KC is a whole new world to me. And being there for the month of July allowed me to understand the types of houses there, the potential issues they could have and what the market was offering. Also if I wasn't there I would never have gotten my first deal. The market is so competitive that most houses I looked at already had offers. The house I purchased was one that I had been watching through a real estate site and it came back on the market while I was there. I made an offer that day and still had to compete with one other buyer.
I'm constantly learning and always reading new material. And you'll hear it said but the more you tell people what you're doing the more you'll find out that other people are doing the same thing. I've had so many conversations with people that I never knew were investors until I mentioned I was. I love hearing about what other people are doing in other markets.
I hope this helped some, I probably went off on some tangents.
Best, Leo