I currently live in the home managing the property, remodeling the kitchen, installing a bathroom and reconstruction to the deck.

Would you want your heart surgeon to be doing your surgery in between shifts at his day job?

The property needs approximately 150k in work between both sides included reconstruction of a 4-story deck off the back of the house that you can see the entire city from, exterior/interior painting, a new roof, new furnaces, electrical panels, flooring, a few windows, updates to kitchens and bathrooms, etc.

You wouldn’t hire the cheapest heart surgeon, etc.

Checks all your boxes; scenic neighborhoods right next to or near the water, the expansive centrally-located shopping/dining complex Coco Walk is nearing the end of it's massive reconstruction, huge new luxury condos just built right across from the marina.

Then gradually, I can do the reconstruction of the house when I have time.

I bought my first home and done major renovations to it as far as getting a permit demolition and reconstructing everything from the ground up.I have three questions:Do I refinance then rent or rent then refinance?

This duplex is being reconstructed due to a fire.  

The Realtor who is their fiduciary, representing their best interest.Your post might just as well read "Not using orthopedic surgeon for my knee replacement - advice needed". 

You wouldn't go to a heart surgeon without referrals...