right now, if you want to buy a portable MD recorder with digi-outs, YOU CAN'T. They don't make any. The ones with USB (NET-MD) will only transfer from PC->MD.
The new Hi-MD's coming out in April will do the transfer from MD->PC, but only certain modes which haven't been tested yet, 'cause they aren't out yet. Word has it that they will have a capacity of 1.5 hours of 16/44.1 (WAV) per disc, or you can use compressed rates from 60 kbits/sec up to 256 kbits/sec. They'll start at about $300 apiece, with discs about $7 to start.
So... If you want MD for stealth, and still want to transfer digitally to your PC, you will have to buy a portable MD and a home deck with Digi-outs. Period.
Or you can wait for Hi-MD in April and take the chance that they will only allow uploads of compressed audio.
(get a JB3)