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Have you tried loading the mag with the cartridges fully forward in the housing? Bullet tips touching the front of the housing is where they end up when you start shooting. They look oddly far back in those pics for some reason.
It could be the left side cartridge that's binding (shooter's perspective). That would prevent the right side cartridge from being pushed up. Get some emery cloth and polish the rails on both sides where case body makes contact. Something is binding in the magazine, it's just going to take some time and experimenting to figure out where.
my money is on a stock - mag box problem. Is the mag box a tight fit in the stock? Relieve the sides of the mag box recess in the stock with a rasp, float or a coarse file. Put a pair of water pump (channel locks) pliers with the jaws inside mag box.
Open the pliers to pry open the back of the mag box slightly. Then assemble and try. Rinse and repeat if necessary. Don't forget to put finish where you have cut the wood when done.