The advantage of "rent to own" is that typically you're selling them an option to buy the property that they can choose to exercise or not.

It's 2021 and I feel that physically collecting a check is outdated and a waste of time and energy.

Certain parts of your system might be things that it would never occur to anyone to do if they didn't start out from the perspective of managing from afar - for example, a house cleaner will usually be happy to do a "deep clean" twice a year and do an inspection at the same time so you can stay in control of the physical condition of the unit.

I'm currently living in the Northeast, but as an independent contractor I'm able to work remotely or schedule physical meetings with ample time to jump on a plane if necessary.

This exercise may enlighten you (and if you want to post your result, I would be interested but I am confident it will be over $1k/month because we buy semi regular, including some poorly timed such as 2004, and they have all appreciated over $1K/month (I believe our worse is $1.6k/month over the hold period)).  

The estimate is just that; nothing beats having someone physically looking at your home. 

I am physically, mentally, and financially ready to seize an opportunity when it comes, but my initial question for you would be: What are some initial steps I can take right now other than running my analysis on certain properties?

I don't blame Landlords for exercising due diligence when hiring a new property manager. 

Now their are times when you may want to provide for a child beyond your life, if they are mentally or physically impaired, but that is not what people are usually talking about. 

I am speaking from past experience- when I have made time to physically sit down with people who are "interested" in wholesaling, none have ever fully pursued it so essentially I realized it is not a good use of my time.