I don't think almond toes are ever "awful." They're classic, and I suppose that could read as dull, if the rest of the outfit weren't current or interesting. And of course, regardless of trends, a person might prefer any number of other shapes, from pointed to snipped to square to, well, round, although for me personally the latter is hard to imagine as a preference -- which the person who adores round toes is going to say only proves "horses for courses," which I guess is my point!
I think the real question is...are the boots still workhorses? Are they comfy? Have they fulfilled their function in your life at this point? Do you have alternative footwear to make the outfits you want to make?
It sounds like the perforated ones have done yoeman's labour and the others were never entirely your cuppa in the first place...if that is the case, let them go!
My climte's different than yours, so boots and booties are pretty much de rigeur for half the year where I live. I am in full agreement that taller shafts are preferable. But I still own 3 identical apart from colour lower shaft booties, though, mainly because I like their other qualities. Pointed toe, good last for my foot, stable 2 inch heel, waterproof, and fun. They may scream 2018/2019 to some because that is when western looks were trending...but then again, they were trending again this year....so for now I am hanging onto them...and on the lookout for their higher shaft replacements.
I like kitten heels but if not well balanced they can be surprisingly difficult to walk on (considering the height). For me, that would be a more dressy item, not everyday. So I think it must depend on the purpose....