I don't know whether or not this might be the kind of thing you're looking for, but I use an Olympus digital voice recorder and its accompanying Mac OSX software. (I have the DS-2 and love it, but there are probably newer models by now.) The recorder itself is elegant, small, lightweight, unobtrusive, intuitive, and so far flawless. It comes with a leatherette belt-loop carrying case--nice. So I'll record an interview or whatever; dock the recorder in its USB dock; it mounts on my desktop; I open the DSS Player software (included in the package); and simply drag the files I want from the recorder to my computer. Since they're encoded as .wma, they can be listened to using either the DSS player or Windows Media Player. Easy-peasy. The quality of record and playback is pretty good, too. I use this thing for everything from interviews to quick reminder notes to recording a funeral for a friend who couldn't be there to capturing soundscapes of a Tibetan monastery at 2 a.m. (blatty Tibetan horns, far-off dogs, and calls to puja). I love this little sidekick! The only thing it doesn't do is transcribe interviews and lectures for me... oh well...
Good luck determining what works for you!