Why not get what you want.

While the classic player is on the way out I still find iPods, Samsung Galaxy Players and more out there. Why would I replace a working player?

As to the phone, this gets too deep too fast. Why? Because with my android phone with thousands of apps out there it's not an issue of the phone. It's that I rarely can find software for folk. I could spend days on that and then the person would reject it because an icon was too pink. So with that out of the way, there are many fine player (softwares) available.