Am I Crazy for Thinking of Stepping Back 9 Years?

Keep what you have and boost the bank roll for the final coach. The Georgetown will go anywhere there's a road just the same as a Dutchstar. The Rockies can look intimidating from the comfort of the homestead but the Steady Eddie will make it just fine.

In five years Eddie will still be marketable at 9 or 10 years of age and shouldn't be difficult to sell privately rather than trading in. The Dutchstar will be pushing 20 candles on the cake which might be a bit more challenging.