If it looks like you can subdivide, then you can sketch out a preliminary plan or several variations to give you a sense of how many lots you can build.     

However, I should note that this tenant has been late paying rent several times recently, which has added some strain to the landlord-tenant relationship.How would you approach this situation?

you're going to be INvesting for the first few years... rental income from the property isn't going to start paying back what you spend in closing costs, rent ready costs, stabilization costs, down payment, etc. for several years at a minimum.hope this helps - not trying to be negative, just realistic. 

To clarify, I have been studying real estate for several years, but have been otherwise engaged in operating  other businesses that my wife and I both own, both as CFO and CEO roles.

Still use paper method for mileage logs.Tried QuickBooks several years ago but it was more complicated and I did not need the bells and whistles.

I’ve learned through experience that if a renovation will take several weeks or months to complete, it’s usually better to hire contractors.

In our experience, things move in ebbs and flows and the speed of rental depends on your asking rents relative to competition.For example, there was a period of several months at one of our properties when a 3 or 4 BR unit came on the market it rented almost instantly. 

He is an investor himself which is great, owns several rental properties and invests in promissory notes, investment funds, etc so he has a lot of good background knowledge in the RE industry that you won't find anywhere else.

Walking score of 95.Pre COVID rental numbers:Monthly gross rent $15,250Cap rate 7.1%Future rental numbers:Estimated Monthly gross rent after current tenants move out $13,950Cap rate 6.5%Because monthly rent looks to be about 20-30% more if you rent by the month, I am considering renting out my duplex for monthly rentals on Airbnb/other sites and potentially for travel nurses (ideal because several hospitals are walking distance to my house).

Maybe if you are doing several transactions a month they would look at it.