Richard, once you get started it's an interesting process and I think you can stay on task if you do X amount per day. That's what I have to do with my father's collection, sooner rather than later. This small task my daughter asked for is just the beginning for me.

Back when Art Thieme wanted to convert his cassettes to CD several Mudcatters supported him in that work (a whole bunch of us chipped in and bought a computer, software, and digital media disks), and I keep him in mind as a role model when it comes to converting files. He finished the work he was doing for the Smithsonian or Folkways people and sent them all of his digitized files.

For most of us it is probably a matter of having the right cables and software. Once you figure out the best routine for you, and I think you can probably remove the DAT deck if you have the right software, it should be easier. I picked up some long cables to avoid having to move the turntable and cassette unit (all together - radio, CD player, Cassette player, and turntable connected by cable) nearer the computer.

Lots of people swear by Audible; I have the Nero suite so I'll work with that before I try anything else.