Welcome to the site. I found bigger pockets from the podcast as well.
We are still relative newbies ourselves on our 4-5 property deal, and just finished the rehab on our first flip (propert is on the market), but I think I can chip in with a couple of comments.
One find a real estate agent who specializes, or only works with investors. You don't want the pretty blue house you want the ugly house that has no paint and has no dry wall. (If you are flipping). They can help you find and evaluate deals, and likely would have good recommendations for contractors.
We started out house hacking a duplex. I highly recommend it. It lets you buy a house using a conventional loan. It lets you learn about hiring contractors and you learn about being a landlord.
as I mentioned we are finishing up our first flip. Knock on wood, I think it came out nicely. But we had a good working relationship with a real estate agent who specializes in flips and rehabs.
But your first time around with a flip, you will almost certainly spend twice what you expected. It will take you twice as long to do. And it will take you a huge amount of time even if you sub out all the work. My wife and I probably spent 15-20 hours a week on picking materials, reviewing completed work, answering questions, finding sub contractors etc. Especially if you are working with contractors you don't know.
Unless you have a good solid savings/ outside earnings and/or have a good background in construction I wouldn't start out with a flip. It's a tough thing to do, and it's really easy to get started and run out of money to finish.
I would also recommend driving neighborhoods that you want to buy in, pick one or two and follow them closely to get to know the area. Know the value in your two mile square target area,better than the real estate agents. You could have an agent set up a MLs email or you could set up a search and look at sales prices in Zillow. That way when a deal comes up you know the market and can act decisively.
We have a house under contract right now in a a great part of dallas. It's a neighborhood my wife and I first started following 5 years ago. We caught some out of town investors who bought the property planning on doing a tear down. But they didn't know there was a conservation district, and they had a buyer fall thru and needed to get out. We are literally getting the house for the value of the dirt under it. And while it's not in perfect condition, the structure is perfectly fine to live in for now. It could end up in the future as a rehab, or could be a college rental, or could be a tear down in the future.
My point is we got it under contract about a day after these investors lost their first buyer and they just wanted out, and we ended up under contract about 30-40k under what they paid earlier this year. But because we have researched the market for several years, we were able to act decisively and believe we have gotten a very good deal in a well known part of dallas ('m ' streets).
Good luck to you!!