Writing Woes

A new assignment of mine is to write about what it's like to write a short story. Without getting into the 'colorful' language I might use to describe it, I will say that it can be very...frustrating at times. I have a problem with deadlines- hate them. They always make me stress out way more than I have to and I fret about finishing everything in time. Often I'll rush to get it done, which is a bad thing; I end up leaving out good details that I would have put in if I just took my time. I have to give myself the time and everything turns out better when I do that.
Another thing about writing a short story is the fact that I have to keep it short. I am notorious for expounding a bit too much on minor details. I want the reader to understand what it's like to be in certain places, but then I end up describing things that no one cares about, like how dirty some one's shoes are or how dusty the floor is or something trivial like that. I like doing those things, but I have to bear in mind that I'm writing a short story and not a novella. I have trouble keeping things concise and to the point. I like to expand on what I write, get as detailed as I can, and even a bit melodramatic in some cases. I like to write about places other than what I'm used to, and if it's some place far off, I'll research it a little to get a feel for the place.
I like to have at least three characters that I work with in a story; that way it's not completely over-the-top and convoluted. I no longer restrict myself to writing from one character's point of view, or writing from a girl's perspective.
It can get crazy sometimes, and I'll go through the editing process numerous times, chopping out what I don't need or no longer like. I definitely avoid cliches as often as I can; nobody likes to read a story and figure out what's going to happen in the first three chapters.
With short stories, it's a little more difficult, because you have to conform to some of the 'writing rules.' It can't be too long, because the reader might get bored, but it can't be too short, because then it's like 'what just happened?' You have to find a comfortable medium between the two, and that's always a pain in the butt.....