depends on context. if its a team match and against someone just random, I resign as soon as I know I have no counterplay and the person knows what they are doing and will not slip allowing me to swindle. if against a friend or someone I know who is learning, I don't mind if they don't resign when I know I am going to win a move or two, and I think you have more leeway in this context in general. it does annoy me if it's in a team match and the person won't resign even though I am going to mate them in a few moves. look at my games vs. a guy named baradzied for example, he could have resigned a bunch of moves ago in both games, but he hasn't, a little annoying to me because it's a team match and he's not someone who is learning, rated 1900 something, he knows he is lost in both games and still won't resign, minorly annoying. actually happens very often on here.
it's good that you are concious of this. a lot of people don't even consider how it might annoy the person and just play on and on and on and on even though they know they are lost and the person is obviously not going go insane and allow them to swindle.
When? How soon is too soon? Is it rude? What is the proper etiquette? A few times I have gotten mad over the terrible moves I have made and just quit, not thinking about how I could just turn the game around and there were times that I was just so sure I threw in the towel too early. Other times I am out pieced and know I will lose, but I make them chase me anyway. I just want to know how do otheres veiw these actions of mine and if there is a proper way to use the resign button. Thanks for your comments.