Hi Nate -
I am on my second house hack now in Chicago. Bought a 3 flat + non conforming last year in Wicker Park and this year was able to get a 2 flat and rehab it in West Town. I am also a fellow consultant, so more than happy to connect with you - DM me and more than happy to answer any questions or go over the experiences I have had.
In regards to education, I did all the same things as you mentioned in terms of reading/listening to podcasts, however the one thing I would say is I've learned so much faster and more relevant info about RE investing by just doing it.
In regards to price point you mentioned above. I think it's a little low for what you are looking for. Either 1) you can get a multifamily at the 500k price point, but you'll have to put in some money in a rehab in order to have the property livable and attract potential tenants at good rents, or 2.) increase your price point and do a little less rehab. There are pros and cons to both - it's all about how much work + $$$ you're willing to put in.
Hope this helps!
Thanks,
Marco