A lot of folks don't take the time to educate themselves on how to do that. 

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.

On the job education! 

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

I'll be losing it, but I'm willing to consider it the cost of education. 

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

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.

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.

Sharing my experience, in my opinion, can help educate other new and experienced investors considering similar investments with ABC Baltimore or having investment discussions with Maverick Investor Group and Hipster Investments.