It is a semi-detached duplex and the layout of both units are the same.

He uses the other 2 garage stalls as storage for his plumbing stuff (almost impossible to walk around) and has several cars (buried in the snow) and even a semi-truck on the property as a storage unit.Our initial plan was to fix up both units and the refinance them separately and attempt our first BRRRR.

I and semi-experienced, I did 2 flips in 2018, I made 15k on the first one and lost about that much on the second, then I got into a car accident and took a break.

I am unsure if this is necessary but would like to hear opinions of more experienced landlords.Any advice for a new landlord in this semi-tricky situation would be greatly appreciated!

At the same time, I'd need this city/town to be semi-insulated from economic downturn where people stop moving to entirely when the market shifts.

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)).  

I’d love to buy the semi I’m attached to as well if it ever came up.

You could just remove the door, and make the doorway opening wider so that a partial wall exists for a semi-private sleeping nook. 

He should know to check his mail within the week time period, deposit the commission check and with mobile deposit its really easy now -- even my semi-bs brokerage is doing it and moving to fully electronic files. 

Between the ring and the smartlock it would be a semi expensive system to implement but it seems like it would satisfy what you're looking for.