Residential Post Light

One of post lights is existing and is being replaced. The uf leaves a bell box that is attached to the house and then goes underground with 1/2 pvc about 3’ from the post light. My guy used concrete around the post mistakenly covering the uf cable. After he is done chipping the concrete, we’re going to extend the pvc to inside the pole where I’ll stick a bell end on it, and then pull a new piece of 14-2 uf. Does that sound fine?
 
I don’t think there is a connector for the 14-2 romex where it enters the back of the plastic bell box. What would you use there for a connector?
 
I don’t think there is a connector for the 14-2 romex where it enters the back of the plastic bell box. What would you use there for a connector?
Actually looking at a picture it looks like someone used a metal single romex connector in the back of the plastic bell box. Would you leave it, or replace it? If replacing what would you use?
 
On the job today we had some hand holes too. I understand the idea of the weatherproof wirenuts, but they’re bit of pain. We were making up some stranded and solid connections, and when you push them into the wirenut the stranded would be pushed down by the edges of the wirenut.
 
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