I've ripped a lot of tapes over the past few years and finally landed on an efficient method of ripping, tracking, and labeling the tapes. It's super simple but perhaps it will help. The TLDR version is:
- Turn on auto record / auto stop on your field recorder.
- Plug an RCA -> aux cable into the field rec device and press record.
- Put a post-it on the cassette shell / record sleeve. Take note of the side, and the filename on the field recorder.
- Keep doing this until the SD card is full.
- Empty the SD and rename according to your post-its.