It's good to do soul searching often. A few months ago, real life hit me all at once it seemed like. I just couldn't justify keeping a single knife. The funny thing is that I liquidated all my knives a few years ago and had just gotten back into the hobby. The one I got recently is up for grabs as well.
There's a lot of thinking in what you said that we all need to do when the time is right. Life has a funny way of throwing curve balls, and sometimes it's those financial curve balls that hit the hardest no matter what we collect. And while it's painful whether we are forced to sell a mint condition "grail" or a trusted user, sometimes you gotta do what you gotta do.
And here's a downer of a thought. What happens to your collection when the unexpected but inevitable end of life happens? While you may know the value and identification of every knife you own, do you have that information to pass on to your family? What knives get passed down to kids, grandkids, etc.? What if your family looks at your collection as a pile of steel and plans to sell it for the first 50 bucks that comes their way, including those high end grails that you paid dearly for? While YOU may know that you're collection is worth in the thousands, to someone who doesn't know knives just views it as something that's taking up space in the house. It won't matter if they're used or not necessarily. Point is as a friendly reminder, keep a record of what you have so that after the dust of your death happens, your loved ones will at least have a starting point on how to tackle what was once coveted by you.
And let's do another downer of a thought on the inevitable.
Use what you love now. Life can be short and unpredictable. Lying in a hospital bed wondering if you'll ever see the outside word puts some perspective on what matters in your world. Been there and done that a couple of times. Wanna know what I thought? I laid their thinking what a shame that those high end, high performance knives that spent a lonely life sitting in the display case will never show me what their potential would be in use. And while using them may decrease their value significantly, what would it matter if I'm dead? So when I did eventually did leave the hospital I went home, took a Don Fogg integral that was a crown jewel in my collection and put it to use. The first scratch was heart breaking and when my dog chewed on the sheath (but far from ruined it) I thought my head would explode. But a dozen years later that knife has been around the world with me and collected many, many memories. And the dog that chewed on the sheath died a few years ago, but I have very fond memories of him every time I look at the sheath. Joy of owning is one thing, but the joy of using what you love is even greater. Why buy a Ferrari and put it in your garage on blocks because you may get a bug smashed in the grill? Drive it. Put a 100,000 miles on it. In the future those memories of driving it will far outweigh sitting in your garage admiring how it looks new. Same with knives.
Getting back to knives it doesn't matter if you collect sub $50 knives or sub $5,000 knives. At the end of the day it's still a knife. The difference is, will it be in your pocket or on your belt, or sitting in a display case? The answer is, wherever it brings you the most joy. ShouldaWouldaCoulda only gets you so far. And for me those knives that trip my trigger are the ones that I want to spend as much time with as possible, using them as much as I can, carrying them as much as I can and enjoying the memories of every scratch and scrape on it. If I'm ever in a position that I have to sell it, I'll take the loss on value but I'll still have the memories of using it and owning it. Knives go away, but memories don't...Alzheimer's willing!
So to wrap up the navel gazing in this post, enjoy what you have. If a knife doesn't bring you joy any more sell it or trade it for something that you'll admire for years. If it's something you'll never own again, forget how much it's worth. The joy of using far outweighs the joy of owning. You'll still own it, but you'll love it even more.