I bought three new Walkmans while they were still making them. I also bought a couple more used one at yard sales later. I have hundreds of cassette tapes that still 'work/sound' just fine. When I mentioned this at my weekly poker game, the younger players let out a howl.
(I could care less)
As a birthday present one year, Mrs. VanShuyten bought a Walkman MP3 player for me and transferred my favorite albums and cassettes to it.
Love that woman.
If you have really good recorded tapes (Those recorded on a high quality home deck from a good source like a pristine vinyl album, NOT most “professionally produced” cassette tapes) will sound much better on a good cassette deck and analog headphones than just about any digital source and especially anything like an iPod. But, that is the nature of things when comparing analog and digital music recordings.
Why do you care at all?