I tend to buy things that solve a problem correctly and add value to my life.
How I spend my money doesn't rely on "what it is" in any way. Is it a "Chrome Extension"? "Standalone Product"? Doesn't matter.
I don't "expect" something to be free, but I'm happy when some things are. But if I find a Chrome extension that is $99, but it solves my problem perfectly, then $99 it is, and I may just buy it.