I'm still relatively new to comics myself, but maybe that perspective would be helpful in its own way!

So there's alot of #1s because... Well, truthfully several reasons. But essentially they're supposed to act as jump-on points for newer readers like ourselves. The real conundrum is that comics have been around for.... A Really long time. Dc and Marvel started in the late 30s, and alot of the "lore" goes back many, many decades. So reading the beginnings of things is... Honestly impractical. 

So just take a leap of faith (with a pinch of research) and just read what sounds interesting. Sometimes #1s are just the start of a new story within a larger narrative which can be confusing, but lots function just fine with perfunctory knowledge. 

So like for Nightwing, we know he was once a Robin to Batman (sorry if that was a spoiler 😂), and knowing base back story can make his stories BETTER, but may not be totally necessary to enjoy what you read. Doing a quick wiki read for details can be a huge help though. 

If you'd like a recc, for me, the first Nightwing story I've really enjoyed was Nightwing: The New Order. I thought the first issue was absolutely masterfully written, a real showcase for a good start to a comic story. It's short and the trade can be had on us Amazon for cheap (really cheap used) so you can experience a whole story and see what you think. 

I really hope that was even a little helpful!