I have many knives, but I tend to carry the same two a lot. I use them a lot, and I like their familiarity so much that it’s pretty tough for another knife to knock them out of the #1 and #2 spots. Happens occasionally, though.
Here’s my take on the issue you’re describing - let your usage decide.
Do your typical daily uses require certain knife features? For (a goofy) example, is batoning enough kindling to start a campfire a daily task for you? If so, then make sure one of your carries will stand up to that task without damage. If you know that you’re going to cut 100 pieces of rope, or slice 100 loaves of bread, consider something serrated and see which of your collection best suits the work. This could be called the “don’t be caught short” approach, carry the best knife you have for the tasks you foresee.
If your average daily cutting is more general or not as demanding, and it’s likely that almost any knife could perform it, you might benefit from the “give ‘em all a fair chance” approach instead. Line up all your knives by alphabetical order, or color, weight, length of blade or any other criteria you choose. Set your goal to carry each one for a set period of time, maybe one a day if you have 365 entries, maybe a whole week if you’re looking at 52. In any case, don’t carry the same one twice until you’ve carried them all once. This plan will give you a predictable sequence to follow, acquaint you with the desirable and disappointing features of each knife, and hopefully cut your agonizing down to a manageable level. Keep notes.
After one year (or other arbitrary period), THEN do the large scale evaluation, and decide what to keep or move. You’ll have a rational basis for your decisions, and more confidence that you’re doing the right thing.
Like Gilbert implied, this feeling is just a hazard of affluence. Many people in other times and places have had only one knife, and worked it hard continually til they wore it out. Then, if they were lucky, they found a new favorite that worked as well. I have a worn out 6” butcher knife from 1906 on my rack, there’s about 3/8” of it left. Somebody used that one hard over the years, but took good care of it. It reminds me that my ancestors did a lot more with a lot less than I have today, and makes me humble about it.
Parker