The ejector spring will wear down at the indent tip that drags on the bolt, when it's worn too much to a flat the spring loses structural integrity and it will suddenly catch/bend/break/seize the gun on a single racking stroke. Depending on the bolt's surface finish/roughness, that wear may take forever or it may take only a few thousand rounds. The bolt's surface finishes on express models is VERY abrasive. I figured out that the best way to prevent the spring breakage is to sand down and polish to a mirror finish the ejector spring channel on the bolt to stop any wear that may be occuring on the spring.
I don't have a wingmaster, but I suspect they have a pretty slick bolt with a mirror finish already, hence the lower rate of ejector spring breakages.
The usual "re-use the rivet" method is a bandaid fix at best to a known design flaw, and the Brownells tools are absolute ####, they almost always crack, preventing you from finishing the job. The smartest way is to file the rivet head flat, drill (without coming out the other side) and tap a hole for a screw that is appropriately sized to the ejector spring hole, and hold that spring with a locktited screw. Obviously, that takes skill, know-how and appropriate tools.
Remington should have revisited that stupid rivet a long time ago.
A lot of people who's spring broke simply end up cutting the bent spring and leave the rest of it riveted in the ejector, and use their 870 without it, as most 870's will eject just fine without the spring due to the design of the ejector.