i learned a couple of months ago that my last year and a half of brewing every week or two could have been simplified by keeping my beer in primary and then bottling from primary.
i started hearing that people keep their beers on the yeast for up to 4 weeks before bottling them. every batch i've made since is put directly into a carboy (not a bucket like i did so many times before) and then bottled right from the carboy.
you don't transfer unless you NEED to (racking beer onto woodchips, dryhopping, etc). with all of this said, i think you NEED to transfer your barleywine.
you don't want to risk having your yeast create weird flavors in your beer by keeping it in contact with dead, spent yeast. unless, of course, you want to be let down in 6 months.
any beer i've made that needs to be aged for an extended period of time (ipa, tripel) needs to be racked to another vessel before doing the extended aging process. once it's racked, you can have it age as long as you see fit.
just remember that if you're going to bottle carbonate, pitch some new yeast in there before you bottle since the yeast will be long gone and will not react to the sugar you throw in the beer.