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A cassette walkman
An all-in-one modern solution for that: https://www.wearerewind.com/
(The Fiio CP13 is better, but it doesn't have recording functionality)
I have a WM-EX631. I dont trust anything made after 94 thats not Sony. 2004 is my absolute cutoff.
I'm jealous, that sounds like a very nice unit. Unfortunately it's hard for me to trust used portable machines like that one if I can't verify they work beforehand. I'm sure it sounds much better than the newer units though.
There is still a trove on EBay and Etsy. They're just expensive. Just make sure theres pictures, the seller mentions its tested, and you have 200-400 bucks you've luckily come into.
The only issue mine has is it sometimes flips to the other side of the tape automatically before reaching the end. Though I think thats operator error somehow.
How do I transfer my FLAC files on to it?
You need a male-male 3.5mm audio cable...
You dont without effort, but theres not really any modern Walkmans that dont connect to WiFi. You are pretty much limited to cassette and disc Walkman, maybe a minicd player. You could burn your FLACs to a CD if you wanted. I've looked at a few modern Walkmans and they are basically shitty android devices, a phone with a 3.5mm jack would be better.