To answer your question, I actually enjoyed how "dated" the show was using pagers, pay phones and the early versions of cell phones. It made for character development.
I will say though the writing is top notch. I won't dispute anybody saying it's one of the greatest shows ever.
To be completely honest, I enjoyed the street shit way more than the other shit. Those scenes were tense and had consequences depending on a certain decision or things leading up to it. It was like watching live action chess.
Nobody really above that got hit with any real life shit except for Kima getting shot.
I was ___ this close to not finishing after like I think the 3rd or 4th episode of season one when Omar got introduced and it started with the "other shit". I was like here we go. Luckily he's so good of a character that his sexuality takes a backseat and morals/code are the highlight for him.
Reading you say that is another reminder of how great and timeless this show is bc it's exactly what i felt when i watched it then. It felt "real", you had smart cops and dumb cops, you had smart gangstas and dumb ones and you enjoy each for what they were.