What a really gorgeous collection, Skater, you have impeccable taste. I am feeling inspired by your struggle, as others must be. It's time for me to divest/cull with an impending move on the near-ish horizon. Nothing quite like moving for making one rue one's Squirrel proclivities. I have HOW many.....
Perhaps as you look long and hard at your lovelies it would be best to think of the annoyance factor, if you know what I mean. Rank them, and it may become easier as you go along: which few, though lovely to look at, have not followed through in their performance quotient when out and about? I suspect we all have different thresholds of how much Faff /Discomfort/Impracticality we are prepared to put up with. For myself, I find mine rather lower these days. Still, I'm encountering that age old nemesis of the culling process, the What If? factor.
Good luck and let us know how you get on