I had one decades ago as well when they first came to the US. Mine was extremely finicky to program. I had hold it very still at a fairly specific distance to my CRT. It was rare for me to be successful on my first try and it was quite slow.
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I noticed that the Datalink 50 and 70 watches (along with other protocol 1 devices) are very finicky, yeah. The Datalink 150 and 150s is much better, although not perfect. The success of the transfer needs a bright CRT monitor, and your room should ideally be free of flashing devices, like florescent bulbs and some LED bulbs.
My Notebook Adapter emulator, with a bright white LED attached, is a significant improvement. It can sync a Datalink 150 watch several feet away! In fact, the light is so bright, that if you hold it too close to the watch, it'll saturate the optical sensor and cause transfer errors simply due to its brightness. If you point the LED sideways, this fixes this issue and makes transfers work just about every time. Check it out:
This picture is from my timex-datalink-arduino GitHub repo at https://github.com/synthead/timex-datalink-arduino! Feel free to make your own!






