I just grabbed the SPM-1000 "Undercover" unit from Radioworld.
Pryme Professional Series Earpieces
At Radioworld it was $65 +Tax.
I have no idea what you would get for $300, but I don't really think you need spend that much to get a decent earpiece.
As far as wearability, I use it for hours scanning. And the PPT button is on a nice LONG wire, that can be disconnected if it gets broken. In addition the PTT assemble has a big housing and button that you can find with gloved fingers, and a metal clip rather than plastic.
That model comes with two extra tips and a few replacement parts.
Also has a nifty gel loop that secures it to the point that it's almost impossible to get it off without using you fingers. Great for those time when you have allot of neck gear on that snags the wire regularly.