Well, I'm on the job market for the first time right now as well, but I can take a crack at answering part 1. I have a compromise on the question of whether or not to include documents which were not required, and hopefully people wiser than me will leave a comment warning me if this is a terrible idea. My compromise is to include within the shorter version a link to the longer version, which is hosted on my website. At this moment, my short research statement is 2 pages and can be read by anyone. The long one is 10 pages and I figure the experts on the committee will go look at it if they're interested in me. I might also do something similar in my teaching statement, because like you I want to showcase my teaching evaluations. My thought is to upload a complete dossier of evaluations to my webpage then link to it within the teaching statement, which is again 2 pages (I have to check with my advisor as to whether or not this is a good idea).
As for whether or not to include too many reference letters, I was recently told that the committee will form their opinion of you based on the average, so if you find yourself with too many letters you should just send the good ones. This was advice for tenure track liberal arts jobs. I think the advice was meant to warn me off from asking random big-shots to write letters for me even if they don't know me very well. This is not a problem I'm having, but I will say that I'm using a different set of letters for tenure track than I am for post-docs.
For filtering, I've heard that the committee looks at your CV first to see if you're in the ballpark, then letters, then either research, teaching, or cover letter depending on the job. Cover letter is especially important if you seem like an unlikely candidate for that job. You need to explain why you want the job and what you'll bring to it.