Lol thanks for pointing that out, I'll have to update my profile.
As I started typing this out, I'm realizing that this is an incredibly valuable question that I haven't actually articulated myself; I've just kind of kept moving the goal posts as I didn't achieve my goal (for example, I just refreshed my goals going into 2024 and I've changed the date for financial independence to 12/31/24).
First of all, I would say it was an ambitious goal to begin with, which I was fully aware of, because I would have had to replace my full time income with rental income within a couple of years of buying my first property.
More specifically though to get at what you're really looking for with your question, I haven't mastered the art identifying and purchasing quality properties that cashflow right from the start. My place here in Denver has been the only property that has made money right from the start, but after that purchase, I had a fixed amount of cash that I could take and either purchase one more owner-occupied property in this area or change to the BRRRR method and ideally continually recycle that cash and continue to acquire properties; I chose the latter option and chose Houston because I was priced out of Denver for a BRRRR with the amount of cash I had. So then I went to one of the cheapest areas of Houston to purchase properties because I was hesitant about purchasing something too expensive for my first BRRRR and losing all my cash. However, one of my properties in Houston is a very low quality property in a low quality neighborhood, and I took some bad advice to try it as an AirBNB. I had a lot of issues with the rehab that my contractor did (overall he did a very poor job) so I've spent probably 3 times what I originally budgeted for the rehab and I couldn't get it rented consistently as an AirBNB. So that property has drained a lot of my funds. I've absolutely learned a lot of lessons, but it came at the expense of my own cash and, more importantly, a lot of my time that I would have spent investing in additional properties. Another thing that didn't help was my contractor. I feel I vetted him thoroughly and he just didn't do good, thorough work; I talked to a few people that had used him before I selected him and got good reviews, so I think finding a good contractor is going to be trial and error to some degree until you find someone you want to stick with (which I have now thankfully after 4 different contractors).
I also haven't learned to use other peoples money, which would have allowed me to purchase a better property in a better area, something that I think a mentor could have helped me with (so I'd also say that I should have prioritized finding a mentor sooner).
Finally, I'd say that the most tangible thing that has held me back from that goal though is buying a quality property in a desirable neighborhood; my most profitable property right from the start is my property in Denver. Even though I live in the basement and rent out the upstairs, people are still willing to pay the value of my mortgage during the lowest points of the off-season, and at the high points I've made close to $3k in profit over my mortgage. I would have loved to continue purchasing in this area, but as I mentioned, I didn't have the cash to do it more than one more time. So instead, I hit the easy button and bought a crappy property in an undesirable neighborhood in the Houston area because it cost $100k to. I actually thought I had done enough research on the neighborhood and the immediate area but I'm finding that it takes a lot of work to truly identify these areas. I should have also spent more time physically in Houston getting to know the in's and out's of the market since I made the choice to invest out-of-state.
So this go round, I intend to take those lessons learned and find a mentor/partner, do my research to find very desirable neighborhoods within Houston (including spending extended time in Houston), and buy properties that need just the right amount of rehab work (has to have good bones).
Thanks again for the question, this has been very valuable to work through in my head!