I know the feeling all too well. I have a super hard time selling pretty much anything; stems from growing up scratching and fighting for anything. I thought about selling off most or all of my old cars and buying something like a used Hellcat, however as I thought it through I arrived at the fact that I already have a 2010 Challenger RT (not a Hellcat obviously but representative of the breed), I grew up loving the old cars, and that once I sold them I would never be able to replace them and I knew that I would want to. In other words, new Challengers will be available for quite a lot of time in the future whereas the old cars won't be.
We all have to do what we have to do. If its not a financial burden its worth keeping IMO.