Best walkman (tape) for around $250?

Lol.. im thinking of actualy doing that.. have a ZX7... and thinking of putting a DR3 in the car

Never owned a Walkman but did use a Nakamichi 250 deck in my 77 Honda.

It's a small top loader that can run off 12VDC.

DeKay

Sometimes just in the mood for that old tape sound. Not trying to compare it to anything or any other format. Have a long trip and sometimes its better than getting A.D.D. with digital songs. Its like vinyl... you feel more committed because its hard to forward a song. Anyway... I was looking at facebook prices... they seem better.

You must be having a lot of cassettes. I am seeing on eBay that they are selling the Sony WM-FX290 for more than $150. I purchased that in 2016 for $35 brand new. If you are not too critical, I suggest look at the WM-FX251 which is listed for $119 with free shipping.
Someone in Japan is shipping a very desirable WM-EX20 for $5130 ONLY!

Why not a grammaphone in the ol’ model T?
Looking for quality to go from headphone out to aux?  If you EVER hear any difference over road noise be sure anf post it for all the nobody's that care.

I just use my phone as a music source in my cars. Two of my vehicles have bluetooth wireless and one just has an AUX input. For all 3, I use either iTunes, Spotify or Tidal as the source for my music. Nearly unlimited catalogs.

Not what you asked, but another option..... Also, don’t need storage for all those pesky cassette cases.

lol.. Car.

Are you going to be listening via headphones while on a nostalgic car ride? Or are you connecting this into your car audio system?

Yea.. prices are crazy. Cant really find info or specs on too many of them. Wanted something for some nostalgic car rides. Have a Sony F1, just wanted to see if there was anything better.

Wow. Just checked eBay and they're going for $700-$1100. 

The first Sony Walkman.

I think the dial on your time machine is off.
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Sorry, OP. Just meant in fun. I'm a bit over-caffeinated this morning.