Whilst the wristwatch seems to have transcended generations and multiple technological disruptions, I can surely see the likelihood of the scenario you paint.
Mentally my answer has been to maybe limit the number of pieces I leave behind, to go for quality rather than quantity and to drive that consolidation in time, sooner rather than later. I figure there should be a place to leave the kids 1-2 pieces, maybe one truly daily beater vs a statement/collectors/investment piece. I have a similar dilemma with my fountain pens albeit on a smaller scale.
Until then, and to reverse the PP slogan, we don’t just buy timepieces for the next generation...we buy them to be enjoyed by ourselves here and now.