I just taught Romeo and Juliet to my 9th graders, and very few people realize that this immense, powerful (and teenage angst filled) story takes place over just a few days, and that R&J fall in love and get married within 12 hours. If Shakespeare was outlining it on a forum, people would probably say he needed to draw it out, allow for more character development... But the rapid pace was what made what happened realistic (the teenagers were being STUPID). I believe all stories should move fast, so you can get lost in the action, but the physical time of it can vary.
I also agree that you shouldn't try and contrive a story to fit a timeline... Just go with whatever timeline fits your story. It's not a lack of skill, it's the TYPE of story you like to tell.