I can really empathize with you on the 'early recording' dilemma. I think people getting into live and multitrack recording now are going to have the easist time of it with all the digital tools that will practically do everything for you (relatively speaking).
I started getting into multitrack recording with an old TASCAM 244 PortaStudio 4-track recorder that I bought from a guy who was getting out of the music game in the early 90's, then I graduated to a TASCAM 424 PortaStudio (still casette tape based) and filled up hundreds of tapes over time, bouncing tracks to maximize the limitations of the format. Really taught me how to get the most out of what I had.
Still have all the tapes but haven't bothered to break them out and listen to any of them since I went digital and never looked back. And even with the digital stuff, you have to deal with format changes as computers get more sophisticated.
And I just laugh when I think of what The Beatles and George Martin were able to do in the studio with their limited mechanical recording technology of the time.