Lee, if you feel the moribund widower could be a goer if he could just wade through the mess at his own place, you could tell him that there are firms which will do house clearing for him. Seriously. He's probably gone from shock and grief to a 'don't know where to start' situation. If he's not supported by friends and family, or they've got fed up with him, then total strangers coming in and sorting out your stuff is the next best thing. They'll charge, of course, but they'll also ensure that items are tipped legally or given to charity.
Sounds like he wants a fresh start, but just can't find the starting point! These people are in the Yellow Pages, and if he has a bit of spare dosh, a 'Ladies That Do' service to do a whole spring clean will probably cost him around £100. That would at least start the springboard for the new life he's probably convincing himself he should be making, four years on.
Also, if he hasn't quite got through the grieving process, there are bereavement counsellors with (if he's over 50) Help the Aged, Age Concern, and so on - also in the phone book. As you found out, it's often much easier for the bereaved (even if it's not that recent) to talk with a stranger than family. Just a thought, anyway.