Can someone help me pick out my first speakers?

As repeated many times here, yo have to hear the end result. I strongly recommend you find a half dozen music selections that you are familiar with then take disks or even song names from known streaming sites, to a store that can provide you with a reasonable approximation of your system and environment. This is becoming almost impossible now-days but once in a while it can be done. I know that in Denver there wasn't one single store that could accommodate me when looking for a new theatre system. Don't take no for an answer. If they aren't willing to provide you with a decent audition, they don't disserve your hard earned money.

Pioneer Andrew Jones Designed speakers is strong contender for your price range. 

Hey gang, I just want to say that I’m impressed with how many of you engaged

with the OP I  attempting to help him

with his $300 budget. Anyone claiming that audiophiles (at least the ones here) should be referred to this post/thread.

@10229 +1

Elac Debut 6.2

If you are near Indy The Audio Solutions has two floors full of new and used stuff. If you get used you can get more speaker for the money.  

I had the Buchardt 400 first models and they had plenty of bass and sounded great. 

Have fun

jh