Hmmmm.. Good point ken. My dad does wear glasses I wonder if that is a deal breaker?
Comfort is a possible issue with any headphone and user dependent. When I was talking about clamping, it wasn't pressure around the ears but a feeling of pressure on the head. It lessens over time with use or you can extend the headband more, and wear them a bit loose which all but eliminates it. Another good idea is find something they can fit on in the first couple of weeks when your not using them so it speeds up the break in process on the comfort.
There are also 2 different pad options you can buy for the 440. The Shure 840 pads which are bigger and more comfortable and the Shure 940 velour pads with are lush.
