One more question...do you attach references, or wait until they ask for them? I also have a letter of recommendation from an old boss. Is it okay to attach that as well?
I've done a lot of this sort of thing, so I'll offer a few suggestions:
First off, I've NEVER had any sort of luck by submitting my resume to a company's web site. I'd strongly suggest you NOT do that and instead, talk to a few recruiters first. What I've found is, a recruiter won't even talk to you if you've submitted your resume to a company's web site in response to a job.
Secondly, if you do decide to submit, your cover letter (and yes, you should write one) should be TARGETED toward what they're looking for and specifically how you can meet that need. It need not be lengthy - a couple/three paragraphs tops.
Your resume should be no more than two pages at absolute most. Why? Because resume readers won't really go beyond the first page anyway, and if it goes beyond two, it'll often get dumped in the circular file. You've got to learn to summarize your job positions.
Dates of employment - gotta be there. If there's a gap, they'll want to know about it if you make it past the first cut.
References - NEVER put them on your resume and don't add that stupid comment "References available on request." If you make it to the hiring stage, they'll make you fill out an application anyway and THAT'S where you record your references.
Phone numbers: Don't preface it by saying "Phone number: 212-123-4567" They know what a phone number looks like.
Email: get rid of the goofy "wannagetlaid@comcast.net" and create a professional-sounding email on one of those free sites like Yahoo or Hotmail. Definitely do NOT use your company's email for job hunting purposes. That's an invitation to disaster.
Job searches are a full time job in and of themselves. It takes organizational ability and perseverance. Good luck!