I've never heard of an editor being afraid to tell a writer anything and certainly never experienced an editor or publisher holding back at all. I've worked with many editors and that's just never been the case for me.
Writing on spec is another journalism term. It's when you pitch a story idea and offer to write it, agreeing that the publisher only has to pay you if they decide to run it. It's basically saying to the publication that if they are interested in your idea, you're willing to do all the work and hand in the story before they make a decision on publishing it or not. If you're not writing on spec and you have a story idea accepted, there is something called a kill fee. A kill fee comes into play when a publication accepts your story idea, but then when you turn in the piece they change their mind. A kill fee is typically half the amount you would have been paid if they had published your story. Basically, writing on spec takes away the publishers risk. When you're starting out as a freelancer (in journalism), it's not a bad idea to offer to write something on spec. That can help you get your foot in the door and give you a chance to prove yourself.
Yup. If you're writing for readers, only what the readers think matters. If you're writing for yourself, you won't have readers so they're irrelevant. The rules exist as guidelines. If you don't know how stories work, then you can't ignore the guidelines and produce anything that anyone else will want to read. They exist for a reason. You have to learn the reason to be able to move beyond them.
