[Gtbrian23]

Matt, personally I will send them an offer originally with what I'm willing to pay. And then when I am down to my last offer and we still haven't reached a point we both agree on I will message them and try to hash something out with them there so I don't run out of offer without getting a deal.

I would say maybe approach it a little differently, maybe say hey I'm interested in your card and wanna work out a deal but before making an offer I wanted to see how flexible you were willing to be. Then base your initial offer on that amount. I say this because people ideas on range for best offer vary. Some people list way high with the intention of coming way down but not wanting to risk missing out on someone that will pay more. But some people list extremely close to what they are willing to take and are only willing to move a few dollars here and there.

This approach may keep you from insulting people insulted by the bottom line question(personally I wouldn't be) as well as give you a ballpark range so as to not insult someone with a lowball offer.

Hope this helps somewhat!