Can someone help me pick out my first speakers?

I'd check out cheapaudioman's review, surprising amount of choices in-budget!

@fuzztone!  I still have a pair of Spectrum 208a!  I just can't get rid of them ....!!

Kanto YU Passive 5.25" for $239 at Crutchfield. They are not audiophile but they rock, The way to go no matter what speakers you decide on is to buy at a place with a good return policy.

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.