I feel like I've said this a number of times but...boy, it'd be nice to know names like the ones that have appeared in the last couple of trades were available.
I think when you're comfortable dealing with someone and can get a deal done that you're happy with you end up dealing with them. Probably not the best for squeezing every last drop of value, but less painful for sure. I generally do the same thing, but that's also due to some managers not returning PMs or providing feedback to inquires. I'll admit I've pretty much written off certain managers because of this.
Oh for sure... there are a bunch of guys that either don't respond at all, or just reject. These guys I am reluctant to even send offers to anymore. Guys that answer (at least somewhat politely) with some feedback are the guys I end up dealing with.
I've seen some pretty bad opening offers that turned into really good negotiations and a fair final deal. Just because I make you an offer that you think is terrible doesn't mean that it's my best offer... and sometimes it could be that I think that a player I'm offering is a lot better than you think he is. We maybe swap that guy out for someone you rate higher and now we're both happy.
There is zero value in being dismissive of an offer. Unless you know it's an intentionally bad offer (you know who you are.)