Point being that property you acquire 1-2 years ago is likely to be subject to deferred maintenance and capex, so their "long term" performance in rankings 1), 3) might skew poorly in year 1-2 but may pickup  after you've found and fixed all the hidden issues.I know if i did this exercise across my portfolio, the recently acquired ones wouldn't be fairly "stacked" because of all the year 1-2 cost build up from what the seller deferred, but have good chances at being future performers in years 3-5.Maybe that's why you have 2) and 5) but curious your general thoughts here are for evaluating this. 

My immediate goal is to acquire our first property and spend the next two years mastering the basics of real estate investment. ( Refining the Go and No property search criteria/ Learning the value of taxes and avoiding them as much as possible/ 1031 exchanges) Depending on my wife’s career orders, we may remain in Baltimore for 1-2 years, but I’m also exploring opportunities in West Texas, Sierra Vista, AZ, and Houston, TX.

Land already acquired and we're breaking ground in the Spring.

I recently acquired my first primary residence and am seeing ways I can best utilize the space for real estate investing.

All properties were bought rehabbed, rented .... 85% of the portfolio was  acquired during the golden years of '07 to 2016.

Now let's look at how you acquire the property, which is a question of capital. 

From there, it requires the ability to conduct underwriting the highest and best use of a planned project, which requires a pro forma built by the user or acquired from a competent 3rd party. 

Acquired 3 lots on mulberry st near west end of Cincinnati about 3 years ago still sitting on it.

It's impossible to answer your question without knowing how much you have to spend to acquire the house.

Your current single-family property has a $1,000 monthly out-of-pocket expense—consider selling and using a 1031 exchange to acquire a multifamily property with better cash flow.