@Scott Tangney I was almost in the exact same position as you about 3-4 years ago. I house hacked a duplex in Logan Square. I probably didn't have significantly more than the 25k you mentioned, but I would say that if you want to house hack in Chicago in a decent location, you'll definitely need more than that to have a respectable amount of reserves after the down payment.
My biggest pieces of advice would be to:
1. If you want to move somewhere else (which is a great opportunity), I'd really think about why you'd move to that location. As much as I love optimizing my returns from real estate and eliminating expenses from living at home, if you find that you hate where you live, it won't matter how good the returns are or how much money you are saving. That being said, I would also recommend to closely investigate whether that location is actually a lot better than Chicago in terms of potential appreciation, cash flow, and lifestyle.
2. Go to local meetups as much as you possibly can. One hour at a meetup can save you 50 hours of later headaches because you met the right person or heard the right advice at the right time.
3. As for educational resources - I would start with Rich Dad Poor Dad, Set for Life, and The House Hacking Strategy. Then I'd read all of Brandon Turner's books (I believe there are four now). I have a ton of other book recommendations not specifically related to real estate, but helped nonetheless, I would be happy to give those as well. I always binge-listened to the BiggerPockets Real Estate podcast, the BiggerPockets Money Show, and the ChooseFi podcast while commuting and other multitasking. As for blogs, I recommend reading stuff by people like Chad Carson, Paula Pant, and potentially Mr. Money Mustache. At this point in your investing, it's extremely important to save as much of your income as possible if you're looking to get into REI quickly.
4. Since you're likely going to be house hacking, I would avoid getting caught up in all the other ways to make money in real estate (AKA Shiny Object Syndrome). Of course, it's useful to understand how note investing works, but it is not useful to put a significant amount of time or money into it when that time or money could be used on your next house hack.
5. From a big picture perspective, if you think you're going to really enjoy your career, I'd focus a little more on long term appreciation vs. immediate cash flow. You'll not only make significantly more in your cash on cash return, but you'll also have an easier time renting to qualified tenants. As an added bonus, you will probably be closer where most things happen in for Chicago 20-somethings. Lastly, like I mentioned above, make sure you have more than enough reserves. The fact that you're reaching out on these forums at 21 means that you're most likely going to win the game of "financial success" at some point. Given that you have so much time and runway, the goal should be to not get knocked out of the game, not to win it 1 or 2 years faster than you would have otherwise. Go slow to go fast, as they say.
Hope this helps!
