Hi Greg.
I would say your problem is heat radiation from the shingles. I have my sensor on a pole about 15 feet above my roof, but my roof is concrete tiles, which radiates less heat than timber. I also have a remote sensor located in permanent shade in another part of my garden/yard and there is never more than 2 or 3 degrees difference between them.
Would it be possible to either higher the sensor or move to another location?
Ideally it would be useful in a situation like yours to use a remote sensor as your main temperature sensor. but unfortunately that isn't possible with VWS. For this and other problems I have been having recently, I am seriously thinking of going over to WD. If I do I shall leave till the start of a new year with a complete fresh start.
Hope this helps.
Alan.