My listings have auto relist 9 times, on all my accounts. I think if you sell over $12,000 in a (rolling) year you lose it. There is also an amount you sell, could be 100 items in the rolling year. It's not 100 sales or $12K, it's 100 items AND $12K.
This has been brought up so many times over the years and everyone that has contacted eBay has been pretty much told the same thing "It's for new sellers only". That is false, because a lot of the long terms sellers were still getting and still do get it.
I have found in the past, if eBay had a promotion running, e.g. unlimited free listings, with so many people listing at once, the tick box would disappear. I would go back a few days later and revise the listing and the box usually reappeared. Sometimes revising via the app will show the tick box if it's not showing up on the full site.
You could also clear out your cookies and cache. That can often help with some eBay issues.
