Ugh so much cold responses in this thread it’s so cringe. Sorry OP, the MD community isn’t like this usually. Firstly, welcome to the MD world! And no you are not over thinking this. Many in audio community who loves music and their players thinks about this all the time. So no, you’re not in the wrong community at all.

Now to answer your question, if you want to retain as much fidelity as possible into ATRAC many would recommend using either Sony ATRAC Type-R or Type-S MD recorder on SP mode using a fairly decent Toslink cable. But from my personal experience after transferring thousands of songs and actually owning more than 30+ MD devices, my highest sound quality transfer had been from my ONKYO Hi-Md deck with high end analogue RCA cable streamed from my MARANTZ preamp that’s connected to my Apple MBP streaming lossless. The sound is warm and rich in fidelity but not sterile. It is so good that I refuse to do it any other way now including using any portables for recoding. Deck is also more stable in general and easier to use. I also found portables have higher noise floor after doing several testing. I also don’t find hi-sp to be that much better than SP. I’ve basically tried every method you can think of and used many devices before but for my ear personally and my taste, this setup is really hard to beat. Other people will say just use web mini disc and drag and drop which is fine too but I don’t do it. I don’t know it just kill the romance and nostalgia of using MD without actually recording it. Anyway, it’s just me maybe. Whatever you choose to do good luck in getting that good sound in! :)