Earlier quoted context omitted.
For radio-free hardware, what about a Palm Pilot? Only has IrDA.
A couple of them had Bluetooth. The only 68k-based one with builtin Wi-Fi was the AlphaSmart Dana, a writer's keyboard. You're very very unlikely going to want to type a truly secure (= long) password over and over and over, which you'd need to do in a situation where the browser's password manager is turned off, and/or a website disables password caching anyway. The Palm m5xx series could solve this problem: it had…
I suppose if you can do full USB, you can probably get data in somehow.