Bigger Pockets is a great place for education and networking. 

PassivePockets is a great place to do this as well as live events such as BPCON every October.Just as important as networking is education. 

Good mindset stuff at the start an great underwriting education at the end.

If all else fails, 😀 ReSure's got extensive resources on all these subjects in our educational platform (which actually includes some plagiarizing from Michael!

Any recommendations you all have in terms of reading, educational meetings, or anything else you find helpful to get a new investor going would be much appreciated.

It may be educated speculation but it's still speculation.

In terms of the second scenario, the upside I see is the option to get a different kind of loan (say, FHA with a lower down payment and other assistance programs for K-12 educators like me) since I'd be getting a new primary residence instead of a second home.

But education starts somewhere, and basic analysis and due diligence will enable the investor to avoid the worst investments.  

Also, I have dealt with 6+ Chicago evictions in one building lolI have learned that if I take all these rough experiences as a badge of honor and share them like you are, each one only makes me more equipped to be a better investor.The education & experience received in 1.5 years takes some investors 10 years! 

If all else fails, 😀 ReSure's got extensive resources on all these subjects in our educational platform (which actually includes some plagiarizing from Michael!