You want to put everything in writing and be very clear about expectations and responsibilities.You also need to verify the remaining tenant can afford the rent.

At this point, I'm not willing to sink the funds for a paid CRM service but may be open to it in the future.

As others noted, most municipalities issue future zoning maps which indicate the direction the local planning commission or equivalent wants to take their zoning and if your plans are consistent, that's generally a good indication as well. 

Quote from @Benjamin Finney: I'm curious what real estate investors and private money lenders like myself use to inform their businesses strategy and predict future market conditions.

In additional to conducting educational workshops, I also write blogposts for their websites.

I know that in the future we will have some sort of market downturns and you could lose all that you acquired with properties that target low paid workers.Behavioral issues are a significant concern.

What factors should I prioritize when choosing the best approach for my future success in real estate? 

Hi Chris from the U.P. of Michigan.Congratulations on deciding to get into real estate investing with your first Buy, Rehab, Rent, Re-finance, and Repeat or BRRRR and you are wondering where to start and who you should add to your team first.It is good you have cash or cash equivalents to buy the property and complete the repairs.As far as who to have on your team first, I would say an investor friendly Realtor who can help you find deals and introduce you to the rest of the team like a good property inspector to hopefully let you know about potentially expensive repairs early before buying the property so you can buy it well or not buy it at all.

Instead of liquidating 1k in the stock, can I just give (transfer) him 1k in stock if he is OK with that (assume he is good with the investment and potential cap gains in the future)?

This could be laborious as a one at a time deal.Not sure if this would work but you might be able to pay someone from Fivr to write a script that would do it automatically for you and generate a list based off of the multifamily addresses that you already have.