I think White Ladder was just of it's time. As you say, the guy was already a long time professional musician, but the musical top 40 climate around then had taken a mellow, acoustic-y trend and stuff like Coldplay, Norah Jones, I Am Kloot, Badly Drawn Boy etc was all over the radio, so his timing for his latest album which was a similar style to what he'd always done (inoffensive, mellow acoustic singer/songwriter stuff) happened to coincide and make his album sell better than he probably would've expected in a normal year, had it not been that mellow music was the fad that year. Definitely not the kind of guy who could carry a large gig, on a big stage in front of a big crowd. I saw Colplay at Bellahouston years ago and thought the same about them. I found the support act, Supergrass, better able to carry the crowd as their music has a bit more get up and go about it. Suppose certain styles don't really travel well and better suit more intimate surroundings.