hi,
If the tape sounds fine while the DAT is playing, I would try one (or a combination) of these:
1. Look at sample rates. For example, if a tape is recorded at 48, and you transfer to 44.1 on the fly, the sample rate conversion may be causing the skips. Import the data at the same sample rate that the DAT is playing (e.g. both 44.1 or 48). Make sure the sample rate of the iRiver matches what the DAT deck (Sony) is outputting. If needed, change sample rate in post.
2. Is the optical (Toslink) connection working fine with other devices (both the Sony and Iriver)? A dirty toslink cable/port can cause bits to drop, and skip. Test the connection with other devices if possible.
3. Just to rule out the head issue, see if the Sony deck has a mode to show error counts, or try playing the DAT on a deck that does output error counts. If the error counts stay low, you will be able to eliminate that concern.
Hope this helps!
