Should I sell my investment property?

[Nicholas Neels]

Hello everyone, first time posting on the bigger pockets forums. 

I have a property that I currently live in near the downtown area in my city. (Windsor, Ontario) this property was bought for $160000 two years ago and is currently worth about $215,000-$220,000. I own four other rental properties, 3 of them in my home town about 30 mins away and another one in Windsor. I am closing on a duplex in my hometown in august and am looking to move in and house hack. One of my single family homes in my home town has a very big lot that I can build a second dwelling unit on, my thoughts are to sell the Windsor property and use the funds to build the second dwelling unit on this property and renovate the duplex I am closing on. Ideally I would like to keep the majority of my investments in my home town. If I keep this property in Windsor I will only cashflow around $275/month but reinvesting would bring me in about $400 cashflow not including the current cashflow from the existing house. I am torn weather I should keep this property or sell it and reinvest the funds into the second dwelling unit project.