When I outline my cookies I always have the problem that one side is always wrong, and is it necesary to outline your cookies before flooding? I've seen some people who doesn't do it and their cookies look great.
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Funny I do the same thing. Must be the right/left brain type of thing. I use a round/square cutter to trace then pipe.. but there are times I don't outline. I think it's whatever you are comfortable with.
I usually have to rotate my cookies in order to get an even outline. If I don't, my hand eventually gets in my line of sight and I can't see how the icing is dropping onto the cookie.
I don't always outline either - in fact, I often don't outline on rounded shapes where I know I want to do a big-ish border. It's faster not to outline, and often I can get a more uniformly rounded edge when I don't outline. I call the method I use (for flooding w/o outlining) top-coating, and I describe how I do it in detail in both of my books and also in my latest video series, which you can find on my personal website.
If I have circle or square cookies to do, prior to baking the cookies, I get another circle/square cookie a fraction smaller than the cookie I was cutting with and make a light indentation with the smaller cookie cutter...that ensures, most of the time, that I will have a nice, perfect circle.
I have not had the guts to do designs without outlining, so I am no help there.
I also started filling my cookies without outlining first. I had tried it several times early on - but couldn't get the icing the right consistency. But once I practiced enough, I got it. It's much easier, and as Julia said - trying to outline there is always a blind spot and even when I know it's coming - it's hard to adjust for it. I either end up too high or fall off the edge! But if you rather outline - when you cut your cookies you can always make an imprint in the dough before you bake and then you have a 'built-in' outline to follow 
Yes I find if I want the outline to be as consistent as possible I need to trace a line. I also turn my cookie and don't outline in one motion. I have just started trying to use the 20 second icing sugar belle talks about. I almost always outline then flood!