Just a Follow up for others searching for a similar solution in the future, I ended up buying a pair of Jaybird Tarah pro's for $140 which I guess isn't too bad.
They're not "100%" wireless as they have a thin wire running from one pod to the other, but I actually prefer this as I can swivel the pods from the wire and have the wire go above my ears and to the back of my head.
So far, with 4-5 runs, they hold in place, the sound quality is all right (probably not close to Bose's but the price tag is much lower and who cares for sound quality when you work out..). Only issue is with bluetooth reception.
My Garmin F645 has to be on the same side as the earphone's receiver otherwise I experience intermittent lags. Thank God the pods can be fully reversed by rotating the pod VS the wire, and inverting the silicon ear pieces. No more issues with reception.
So far I'm happy!
Thanks guys for your suggestions!