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.
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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.
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.