thescruff
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I'll try and get my head around the drawing.
A, it all looks wrong, so I'll do some imaginary connecting.
What is the blue pipe from the store running alongside the flow, and where how does it connect.
Where does the HW return connect, I assume by HW you mean the cylinder.
The pump should always be off when bleeding.
If there's an airlock say in the flow or return pipe leading to the bleed rad then water will still come out the other pipe so you need to shut one valve to draw the air out. so, if the return is airlocked you need to turn the flow valve off, or vice versa.
Your plumber needs to sort why it's pulling air into the system.
Guessing at this time but it looks like you may have cross connections that are causing a backflow or short circuit
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