SR60 probably is the better headphone, for simple economics: All of the headphone's budget goes towards the audio part, whereas on a BT headphone compromises must be made to account for the electronics.
I wouldn't bet on it. On ear and over ear need quite a different tuning. On ear vs over ear is a bit like earbuds vs IEMs. They kind of have a place but from a tuning standpoint they can fall short a lot.
Openbacks are definitely the better choice for sound quality. However, you mentioned something for work use too. If you mean in an office environment with people around you, full openback cans might not be appropriate because of the sound leakage. I have the AKG K240s and they are semi-open back. That might be a good compromise because they don't leak as much as long as you listen at a reasonable volume, and they're around $70.
I wouldn't consider myself an audiophile but the Grado 60x were probably the best sub-$100 headphones I've ever owned. I like how open headphones sound and used them at work because I didn't want to miss it if someone was talking to me. I worked in a fairly quiet office, though so if you are in a high ambient noise area it might not be your best bet. I'm currently using the Sennheiser Game One (Game Zero is the closed version), because it has a mic. I got tired of having to take off my headphones and switch to my phone headset twenty time a day.
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