@Michael Plante I agree with St Pete, FL area but not too familiar with NY markets.

My husband and I are pushing hard to learn all we can and to grow our family assets, while still having time to enjoy our three kids and show them the world.The market here is very inflated and opportunities for solid cashflow suffer as a result. 

You don't want to both focus on it and have the business suffer. 

If the country goes into a recession, these properties will suffer. 

Build an ADU that is of same exterior architectural and eye pleasing as the current house to add value also think about landscaping and plantings that create privacy and sound barriers

Here is an article about valuing multifamily real estate.What you asked for: (pros and cons of holding onto the small multifamily)Pros:Easier to manage yourself with less unitsAbility to diversify where these properties are and minimize risk (one property suffers, others can help carry the expense)Invest in each property as needed, able to spread out expenses over a long period of timeCons:You are not able to scale as quickly as 1 large MF unitHarder to self manage - expense for management feeYou will have to replace 5 small roofs instead of 1 large roof (this goes for A/Cs, Furnaces, Water Heaters, etcThere are a lot of pros and cons to both.

@Jonathan Plant I love that style duplex.

@Luke Jackson - do some research on the timber industry.....https://www.google.com/amp/s/www.wsj.com/amp/articles/thousands-of-southerners-planted-trees-for-retirement-it-didnt-work-1539095250

I have had buyers ask to either include or buy plants, furniture, lawn mower/lawn equipment.You can ask for a new kitchen and bathroom, HVAC, etc.  

I always take the attitude unlike our friend here Michale Plante to treat others like I want to be treated.