I say very carefully ... You know the area and conditions more than anyne, so I am just thinking out loud from what you've told me...
Not in the bedding area, but his entrance/exit areas to food or bedding... I might would try his known travel/escape route... Either of those areas where your blue line segments meet as long as I had the approach and wind in my favor... But older bucks are tough for a reason and even when I get close, he wins more than I do... So take it for what it is worth...
Good Luck!!!