Any way to monitor if 802.11r is working?

You can enable debug level hostapd log and check syslog for below messages.

IEEE 802.11: authentication OK (FT)
WPA: FT authentication already completed - do not start 4-way handshake

Client should start 4-way handshake only when it first associating at the AP and when steering/switching over same SSID, it should be 2-way handshake FT (802.11r fast transitioning) stating in above messages.

edit: yes you just click on enable 802.11r but when doing on different devices just make sure they have the same mobility domain, as well as same SSID and password set.

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