45ACPete:  The OAL of your reloads may be part of the problem.  An original Krag military round (FA-1898), I just measured, had an OAL of 3.060 inches.  My Lyman Manual gives a max. OAL of 3.089 inches for .30-40 Krag.  Also, I would take a good look at the tip of your Krag's extractor.  Does it appear chipped or reshaped?  It is not working right.  A Krag extractor should easily lift and snap over the rim of a chambered round as the bolt is rotated closed.  Look again at your Cutoff with the Side-plate removed.  With the Cutoff lever 'up' the flat on its shaft is down and clear of the feed-path.  With the lever 'down', the round part of the shaft becomes visible and blocks the first cartridge rim to prevent feeding.