According to my reference your first two Canadian paratrooper wings are definitely post WW2 and worn circa 1951 through 1971. One of the ways you can tell is by the backing material. The first has that heavy tight weave shinny dark material and the second has that shinny (starch) open weave dark backing material. The second two are probably earlier pieces but also post war. The problem with these is that they were worn during WW2 and continued to be worn after WW2. With these I believe if they are sewn on a particular way they have a better chance of having been worn during the war. Normally the wing tips arch up slightly. If they were sewn on a uniform with the wing tips stretched outward eliminating the wing tip arch and have retained this shape having been sewn on for over 70 plus years I believe they are WW2. However they were also sewn on with the arch during WW2. The only way to be sure is with provenance as I have one in my collection which I obtained from the person you removed it from a WW2 uniform and it was stretched out and padding added underneath. This has been my observations over the years. Your last piece looks like a WW2 shoulder sleeve patch as I don't think they were worn after the war but I could be wrong.
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