Hey @Matthew Norton!
Welcome to BP! I can relate to your desire to want to house-hack a property. I purchased a 4-plex in Old Louisville in November 2018 and have been house hacking it ever since. The rents from the other units completely cover the mortgage, taxes, and insurance on the property each month. It's amazing how much more you can save when you don't have to worry about a rent payment!
As for the questions you listed, have you considered attending local investor meetups? There are quite a few in town where aspiring, new and full-time investors come together to discuss real estate related topics. It may worth checking out a few to develop some connections.
One of the nation's most popular investor groups, R.E.I.A (Real Estate Investor Association) has chapters in most major US cities. Our local chapter has over 700 members, many of whom are extremely active in the market and have a wealth of knowledge they're willing to share. They usually meet the last Thursday of the month at Wood Haven Country Club but have moved online since the pandemic began.
Along with that, my friend @Luke Neubauer and I also run a local investor meetup group called the "Louisville Real Estate Investor Meetup". As part of the event, we network with other like-minded investors and host speakers who talk about topics related to real estate investment. Since April, we've been hosting our meetings virtually and have been getting solid engagement.
This month, Brian Hennessey, a top commercial broker in L.A and best-selling author of the "Due Diligence Handbook for Commercial Real Estate", will share his story about how he got started in the business. Along with that, he will explain how to properly perform due diligence on a potential investment property and share various helpful strategies you can use to add value to real estate.
Here's the link from the "Events and Happenings" page of BiggerPockets:
https://www.biggerpockets.com/forums/521/topics/830198-performing-due-diligence-and-adding-value-to-real-estate
I hope this helps and maybe we'll see you on the call!
All the best,