Question: Is heading from the Strait of Belle Isle towards a point about 200 miles south of Cape Farewell, then heading towards Reykjavik, a practical strategy given your experience with wind, weather and ice?
Answer: I have never sailed to Iceland without stopping in Greenland, so have no experience with this strategy. I think you are wise to give Cape Farewell a wide berth. The tough part might be after you round Cape Farewell and head north, when you may get on the wrong side of a low and have some pretty miserable weather on the nose.
I would want weather fax on board to watch the lows coming through and try to get on the right side of them. Also, give the southeast coast of Greenland a wide berth since it could very easily become a lee shore in a northeaster if a low stalls in Denmark Strait.
On the bright side, July is about the best weather all year and if the fun really went out of the trip you could always crack off for Ireland or Scotland.