I believe most of your questions are answered in the various PhotoSource materials, but it's been years since I mailed anything. Even when the images are transparencies, I now scan them.
If I believe I have what an editor wants, the last thing I want to do is allow someone else to get their attention before I do. So I make sure to get something in front of their eyes as soon as I can. If I need more information, I can pursue that too, but I need to let them know that I have what they're looking for.
That said, I don't load up an email with images. I may include one or two of modest size to get their attention, but I provide links to higher rez and possibly a larger selection. Then I post those images to my web site where they can look at them at their convenience and with a browser - which is far better than most email programs for viewing images. I also avoid overloading them with a lot of similars, which I've seen some people do. You have to be your own critical editor.
James Cook
Creator of:
METAmachine
FindAPhotographer