If your sizing die is doing what it should, your cases will feed reliably. I've reloaded for 30 yr and have never had a sized case not feed or chamber properly unless the rim of the case was deformed but this will normally show up during your sizing process.
If you use a Dillon press, you will have to set another press up for your second sizing operation since all four stations of the Dillon are already occupied by other dies.
I would also be a little concerned that your second sizing operation might loosen your crimp a bit but, having never tried it, I wouldn't know.
I really don't see the need for a second sizing.
Yes, you should roll crimp handgun cartridges, especially magnum revolver cartridges. Bullets will tend to walk forward in your cases from the recoil of a heavy load in a revolver and they can prevent the cylinder from rotating.
A taper crimp should be used in a semi auto handgun.