i went through this exercise a few months ago, and it comes down to this. You either have to be prepared to drop a fair bit of money or use some crappy stuff.
I tried the SanDisk Clip Sport Plus Bluetooth MP3 Player for the player, used it for a few weeks, and returned it becuase it just didn't compare with the apple shuffle i have been using for ease of use, streamlined design, and looks. I was very disappointed - the thing is plastic and clunky and took too much time to get to connect to my earbuds every time.
For earbuds i got Jaybird x3 wireless sports earbuds. They are really nice and i still have them. They aren't cheap.
So, i don't use the bluetooth setup for running. If i did, i would probably look at something like the Nano model that is bluetooth capable.
Using wired earbuds isn't so bad if you just tuck the wire under your shirt. And it sure is fast to fire up the tunes and go, and to use once you do.