If you get some windows app, it's possible that you will be able to run it on Linux.

If I can get it to run, licensing shouldn't be another road block

That's emulation. Apps don't just run anywhere without you doing this.

In a parallel universe there's an Apple equivalent of WINE. It'd probably be called CIDER.

It exists, it's called darling: https://en.wikipedia.org/wiki/Darling_(software)

It's never been as reliable as Apple platforms are way more of a moving target, so it's never got as feature complete and dependable as wine

No, but I'm sure you're aware that publishers/developers can make versions that run on each platform and license them in more consumer-friendly ways. I've bought non-SaaS desktop apps that come with license codes for each platform. If not included, there's often a discount for buying licenses for multiple platforms. And this doesn't require me to create an account for phone-home license validation. That type of license bundling is not so easy* and definitely less common with walled gardens.

* - I am taking developers at their word on this. I haven't sold anything on the Mac App Store.

That's an extremely rose/favorable look towards Apple which is doing everything in it's power to put itself into the relationship between a developer and a customer (to charge 30% and limit, limit, lock, block). Thats very evil.