Per Samsung DeX's technical documentation, it uses standard Android APIs, which makes supporting it theoretically seamless. Does Chrome OS use the same APIs? What's the difference in difficulty and complexity of developing an Android app that supports one as opposed to the other?

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Per Samsung DeX's technical documentation, it uses standard Android APIs, which makes supporting it theoretically seamless.

I would phrase it more as that they support the standard Android 8.0+ freeform multiwindow implementation.

Does Chrome OS use the same APIs?

Chrome OS uses freeform multiwindow as well, though they backported it to work on Android 7.1 (which is what Chrome OS is using for Android as of when I am writing this).

What's the difference in difficulty and complexity of developing an Android app that supports one as opposed to the other?

In terms of window management, they will be fairly similar.

In terms of Android basics, they will be fairly similar.

However, both have their own distinct differences from stock Android (and each other). For example, with DeX, devices move in and out of DeX mode — a Chrome OS device is always a Chrome OS device. Right now, DeX devices are phones and tablets, possibly using an accessory to enable DeX mode and allow for connecting keyboards, mice, and monitors — Chrome OS runs on notebook/netbook and desktop ("Chromebox") form factors, as well as tablets. And so on.