I understand the soul searching as I have too many cars sitting around that don't get driven enough and every once in a while I think about getting rid of something for a new car. But I would have a real hard time getting rid of my 66 427 coupe that I've owned for 30 years and restored from the bare frame up. Plus a 62 was the end of the line for the C1 series and for an early one it doesn't get much better than that.
Usually after I consider the price, registration & taxes, daily-driver insurance costs, annual property taxes, depreciation and the constant fear of the first scratch or chip for a new $70,000 car - I get over it.