On the hunt: Haggling

[jshepard]

Hey guys, I'm getting ready to start my "hunt" on another watch. I'm looking at a few Rolex models as well as looking into JLC. I'm in the process of doing some research on a few models (Rolex being easier to research compared to JLC). I'm going preowned this time around and I'm looking into some ADs, grey markets and in the classifieds of different watch forums. Anyway, I've never haggled before (I've never been in a position to do so, and I assumed
you'd be a fool to not try when possible). So here's the questions:

1.) How do you start? Do you simply ask how much they are willing to give or do you go?
2.) Would it be an insult to start low (how low is low-balling anyway?!) expecting that they will counter anyway?
3.) How much big of a discount from the original price could I respectfully start with for a Rolex or JLC (I hear JLC doesn't retain it's value compared to a Rolex)?

I hope a don't come off as an a-hole in this post haha, just trying to get the best price without seeming like an a-hole to the seller...