First plan for a new bike in the future. Year or two out. There are not many available now and you may settle on something because it’s available. Then in a couple of years get buyers remorse. Maintain and ride what you have. Sounds like a good fit with the distance you can ride. I have a 2005 Madone so yours is not old.
Anyway I’d go ahead and get a new chain and measure tool. Just to have when you need it.