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As srm wrote, I'd leave that gooseneck bearing alone. Some other ideas below. Sorry if they seem too obvious, but simple is often better. Don't mean to offend, but first things first...
Are you sliding the gooseneck into the track with the outhaul loose? Tight outhaul forces boom forward cocking gooseneck at an angle, and even that slight additional friction can make it a PITA.
Any sign of track being pinched so that it's too narrow?
Perhaps there's some galling inside the track from the bearingless gooseneck's prior resistance to being forced through there? If so, I'd sand out those burrs (wrap paper around a pencil/dowel or such), clean it up good, and hit it with some dry lube.
_________________ Jerome Vaughan Hobie 16
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