I can definitely relate.
I sat out upgrading my 2017 iPP 12.9" because I couldn't justify the cost of the newer 12.9" when the software itself wasn't really improving greatly enough to change my usage. When I bought into my old 12.9" iPP the pricing was low - I had gotten a discount from Verizon on it and basically paid $850 for it (cellular, with 256gb storage). Now, an equally spec'd 11" cellular goes for $1050 and a 12.9" goes for $1300. Adding case and pencil costs to either one just put the upgrade into a range that wasn't palatable for me given what I was using it for even though I have the disposable income to buy one.
Eventually I ended up getting a Surface Pro 9 and a Mini 6. The old iPP is just sitting on the side now.
It's not entirely the devices' fault, it's me and my workflows that result in a lack of needing one LOL. An iPad Air might be in my future at some point as a slightly larger content consumption device than the mini, but for now I'm good with what I have.