askamanager.org is one of my favorite blogs. I think you could get some good advice there, either by sending the question in to Alison (the blogger), or by posting in the Friday open thread to ask the community for advice. The tone of the conversation there is similar to what I find here.
As someone who's hired many people, here's what I'd recommend for your situation:
Summary - get rid of what you have there. It's just a list of buzzwords. You can't really analyze those qualities in yourself, and you are expected to have them all anyway. Replace it with something like "An experienced professional making a transition to office management and executive assistant roles. Skilled at managing executive schedules, handling phone systems, organizing meetings and events."
Technical Skills - this part is ok, though I might get rid of the word "computer" in the first bullet. Can you add something here that demonstrates some of the qualities you listed above? Do you have MS Project experience? Skills at organizing and managing large events, conferences, meetings?
Recent Work Experience - list the last 10 years worth of jobs. No more. Don't try to fill in any gaps. Just put the actual month/year when you started and ended each job. If something was a temp/contract job, put that info as "(3 month contract)". Under each job, list accomplishments that show you have the qualities in your current Summary section. Here's where you demonstrate that you are detail oriented by listing some achievement that required great attention to detail, or that you can multi-task by listing the fact that you simultaneously coordinated 3 different projects, etc.
Write a separate cover letter explaining why you would be great at the job you're currently applying to. This is where you show that you have good communication skills.
If you've only been unemployed since last July and your last job was a contract role, you don't have to explain that gap, it's just not that long, and it's quite normal for hiring managers to see gaps of several months between contracts. If you really want to, you could always say in the cover letter that you're looking for your next role after working a few contracts and enjoying some time off.