Congrats on the retirement and I hope you get to enjoy every minute of it!
Of the bikes listed as keepers (13 total by my count) 11 are similar (fast, road bikes) and 2 are different (Pashley & the errand bike).
What about deciding to re-home all of the maybes and non-keepers and the really trying to determine the differences in the remaining 11 road bikes?
Have each fill a specific role and try and shrink the number further? More focus on riding and enjoyment rather than what I do when I have too many of a thing which is look for reasons to continue to to build/tinker!
Regardless, congrats again and great collection of bike to look at from afar.