I did NOT start hearing these kinds of details until I upgraded my playback.
All true of course, but one of the things I wish people would get away from is nit-piking on the methodology and/or technical discussion used in making the comps. Tech info is relevant, of course, but most comps end up mostly being conversations about why the comp may not be a good comp, which IMHO kinda sucks because usually someone has to go to quite great lengths to set up a comp and then post it onto the site. The last comp I did, literally the first comment asked was a very basic doubting of whether or not I'd set up the mics correctly. That shifted the entire thread conversation immediately into a new direction rather than having the focus be the comp itself. As if I'd go to the lengths to set-up, master, and then post a blind comp only to get something so fundamentally wrong with the comp. I had to spend a page defending my comp methodology and there was literally not a single comment on the comp itself. Totally wished I hadn't posted the comp at that point, got pissed off and took it down. (I can't help it, I'm a sensitive guy LOL.)
If you're still in apartments, start with a entry level DAC/headphone amp and some decent cans. You don't need to break the bank IMO. Look on Facebook Marketplace, the amount of people who tried (and failed) to start a podcast or home studio are endless these days.
I wish I had a listening room. But yes I agree with you for sure that the playback system is every bit as important as your recording system if you want to get the most out of your taping gear. My preference is open-back cans, but my wife has great hearing while I wear hearing aids so even when listening through my Sennheiser 700's (without my hearing aids), she's constantly telling me to turn it down HAHA.
My most common listening scenario is either my closed-back cans or IEMs. I have a decent quality DAC that I can't remember the name of, but I've come to the conclusion that the quality of the headphones is more important to my system than the DAC. (Comments welcome.)
That said, for A vs B comping, I don't think it's quite as important to listen through a top-level sound system since you're listening for differences in the two samples. Obviously subtle differences might not be obvious on lower quality systems, but basic impressions have always been what I'm after when I post a comp. I mean, if two samples are really close, I can't tell a difference if you separate them by 5 minutes anyway, so I personally don't concern myself at that level since my audience recordings aren't perfect to begin with.
I'm not arguing, just offering some thoughts I've had over the years.