On Thursday, August 3, 2017 at 10:52:23 PM UTC-4, wrote:
I have a 2006 Chevy Express van. The radio is the stock Delco AM/FM radio.. All my music is on cassettes

I think you're asking the wrong question.

I have an old (1991) vehicle that I use for local transportation in the knowledge that I have one year left. (each year I decide how much to spend to pass inspection. I'm not planning on 10 years.)

It seems you've decided your cassettes are worth keeping for another 10 years but your vehicle has one year left so you need to be cheap. In fact it's probably the other way around.

My wife put an aftermarket radio in our other car for a trip. It has this weird slot my daughter calls a USB. All their music is somehow on my daughter's phone, in some kind of digital fashion I don't understand but apparently doesn't degrade or tangle like cassette tape. There are local car audio shops everywhere that do this kind of thing and it's not super expensive.