It depends on whether or not an attraction is still achieving its goal. Pirates of the Caribbean is meant to be an exciting journey through ship battles, port towns, and caverns inhabited by corsairs with some unexpected drops along the way. That's still what you get. Country Bears is meant to be a musical revue of recognizable country songs reimagined in a humorous way. The "recognizable" piece is missing and was part of the original draw to better connect with the older members of the audience.
This is nostalgia based on when the Country Bears actually were more relevant. Tex Ritter as Big Al singing "Blood on the Saddle" is only quintessentially Disney to a seasoned parks fan. When I go with people who have never been to WDW before, they don't really know what to make of it, don't particularly enjoy it, and definitely don't equate it with Disney as they understand it. If it included songs they could potentially identify (even just contemporary country), there would be a higher chance of them connecting to it in some way.