Contractor burnout is another concern.Owners like to think it's so easy to just pick up the phone or send a mass email to get contractors beating down their door to give them a bid and hopefully get the job.Doesn't work that way!

What are the pros and cons of each option and in what scenarios would you pick one over the other? 

There is a lot to understand, so pick up a good book. 

I have STR investors in Florida making 25% cash on cash returns, long term rental investors picking up properties directly off the MLS and cash flowing day 1 in various states, and house hackers completely removing their housing payment from the picture allowing them to save for for the next property.The beautiful thing about real estate is there are so many ways to succeed and a plethora of strategies depending on your comfort level and how active you want to be.

One thing I’ve picked up from years of managing rentals in San Diego is that organization is everything..

that's important - a lot of folks want to pick a property on Zillow and buy it just to "do a deal." 

I've used the rental calculator enough now where I think I can find a few 2-4 unit properties that can cash flow at least $100 a unit even with zero down, though the pickings be slim at any given time.

@Matt Powershello. pick a place where you want to live, and house hack there. 

I wish I could find someone local that I could sit down with, like the old days, and pick their brain on how to effectively edit and upload videos to YouTube.

or even more.not saying you're considering going that far out but just using an example that i can speak to.my actionable step for you after picking a market would be: make a trip to that market every month and network in person.