Given a choice, assuming no room behind the board, etc. I'd go with a nice stub up to the ceiling, then install a good sized trough, like at least a 6X6 and then raceway to the enclosure. I'm more of a fan of leaving the service loops in the trough.
I'm not a fan of having to manage a pile of cables in finger duct....it looks nice until you start breaking out cables and the like into different locations and knockouts. I hate the juggling act with the cover, fingers and then watching them snap off when they age....not to mention the miters and related to get to all the knockouts on an enclosure. It has it's place, but I prefer hard piping to enclosures.