My very first introduction to anything "old" tech was through the TechStuff podcast[0] (re: 2011-era episodes, so sort by oldest).
More recently the On The Metal podcast[1] has been a really cool deep dive into old tech history, especially the episode (season 2) with John Graham Cumming.
About implementations, my first real playing around with assembly was "Learn TI-83 Plus Assembly in 28 days"[2].