I commuted from Reading to HW for a while and the drive is a nightmare. The A404 gets really clogged. If you could move to the north side of Reading there is a route through Henley which is fairly ok as you can keep moving and not stop.
There is a riding route but slightly elongated.
As for living in HW – not really it’s not that nice. Have you thought of Marlow? Or Wokingham which is nearer to Bagshot and on a London line?