Nomad or Corpo for me.
First one I did was Nomad, which worked well as I knew nothing about Night City or the gangs. Ofc the beginning is quite well done but as its only a prologue it doesnt matter that much in the long run.
I then tried Street kid but while some Street Kid dialogue options were absolutely spot on, others werent. You interupt a deal going on and get a Street Kid dialogue option that really works for instance. But then later you'll end up in dialogue with Johnny who explains the city and V will sometimes react rather naive. Despite being born and raised in NC. The way you meet Jackie in the SK character background is weird tbh. Sorry that its vague but I dont want to spoil it for others.
While the Corpo start and playthrough had most useful dialogue options in my opinion. The beginning is interesting for the insight it gives into that world, one you dont get anywhere else in the game. So I do like the Corpo background aswell.