Ok so I had the CH700N’s. I also then had some AirPod Pros for a year. I recently upgraded to the Sennheiser Momentum 4 over-ear and the Sony WF-1000XM5’s, but I also bought and returned the WF-XM4s, Bose QCII in-ear, and the Sennheiser Momentum TW3.
Every single pair of in-ear wireless earbuds I’ve tried that aren’t AirPods Pro suck. I am still using the XM5s but their multipoint sucks so I had to disable it, and they drop out for a split second every 10 or so mins. The XM4s were similar but incredibly painful to wear. The QCII were similar to the XM5s. The Sennheiser TW3 connection quality was dog shit - putting a few fingers around an earbud would break their connection with each other.
As for over-ears, my Sennheiser Momentum 4s are pretty good - they sound great, feel pretty comfortable, last for ages, and do not suffer any connectivity issues in my experience.
But to be honest, I’ve reached the point where if phones still just had bloody headphones jacks I’d use wired over-ears. I’d probably still use AirPods Pro for portability once I move back to iOS though, but I could also see myself going wired there too to avoid the whole wireless hassle and cost.
So my conclusion is over-ear for every possible reason except absolute portability.
I also would recommend against the Sony WH-1000XM5 over-ear because they feel so cheaply made it’s a joke.