Should I sell my truck?

I am 25 and I have a 95 Ford F150 I have been driving since I was 16. Now, it is a nice truck. Really well maintained. It has leather and wood and almost every luxury option that was available in 95. It is 4x4, has the 5.0 V8 which runs strong and sounds good too. I also have my custom sound system. I think I have the best truck of all time. Other people tell me never get rid of that truck. But I keep wondering if I should buy a newer car. I also have a ton of money. I am interested in a 2015 or newer Subaru Outback. Would be a good, capable car but practical and I could drive Lyft or Uber. I also have a 1970 Chrysler 300 convertible that is my main project. It is a car that I truly will never sell. But I only need one project. Lately the Ford has had some issues. It's idling high possibly due to all kinds of vacuum or gasket leaks, and the timing is likely off. It just makes me wonder if now might be a proper time to move on from "number one."