Should I convert my site to WordPress?

[bobo.cx]

Hi there,

I'm new to this forum and this is my first post. I hope someone can help me. I have designed this site (www.flexography.org) and at the time, I created some parts of the site with the intent to improve it's functionality later. It's now "later". If you go to the site, on the home page you will see a "Press Releases" section as well as an "Industry News" section further down the page. Those show the most recent top 5 or so stories/releases that have been added. If you go to any of those particular stories, you will notice that I have basically created a new web page for each and every story/press release. In essence, that ends up making my site eventually grow to hundreds of pages. Cumbersome, I know. But when we were pressed to launch the new site, this was the quickest way to execute those stories on the site. I want to make this better. I was thinking of WordPress. Now, let me give you some history on things:
1. I'm a graphic designer first, and a self-taught web designer second. So I'm not as strong in web design yet as many of you are and I'm open to learning new techniques. It also means that I may not be doing things the most optimal way and I'd love to get feedback.
2. I use Dreamweaver and my coworkers use Adobe Contribute to update the site with revisions and new content. They are in a different physical location than I am. I am the admin on all of this. We like this workflow and it works for us.
3. This would be my first experience with WordPress, so I can't envision how things will work for us if/when we convert over, since I have no background in its interface.
4. I have found and have been training myself via lynda.com videos on how to convert our site to WordPress and keep the same look as what we have. I have not started the process yet because I need to be SURE this will work for us before I make the leap.

Okay, with all that background, hopefully you can help/advise me on the following:
1. Can our site be converted to Wordpress and maintain the look we currently have?
2. Do I need to convert EVERY SINGLE page of our site to WP, or just the ones that utilize the new story/blog type function?
3. Will WordPress still work with our Contribute workflow? I know that it will work with Dreamweaver, but I'm the only one using DW and I'm not the only person who edits/adds content to our site. At least 3 others use Contribute regularly.
4. Can you suggest if there are any other options available to me that will automate some of the things on our site; such as the "top stories" thing? What would that portion of our site look like if I convert to WP? A big long thread of blog-type entries? See this page: http://flexography.org/06FLEXO/indnews2012.php. This is the page the contains ALL the links to this years' stories. Each link then has it's own separate page. And the editor then updates the home page with the top stories and links to their respective pages. Cumbersome.
5. We are going to be adding a "members only" portion of the site that will require registration and log in with content specific to members. Will that be possible with WP (or whatever else you might suggest)?
Rosetta Stone Greek Rosetta Stone Italian
Thanks so much for your help! I hope I gave enough info to help make my situation and goals clear. If not, let me know and I'll respond.