New to Press. Will WP work for me?

Hey Everyone!

I’m new to this forum so forgive my ignorance in advance. I’ve been debating using WP as a CMS for my website(s) for a while now. A little bit about what I have explored thus far, I’ve gone through Drupal, Plone, Fire CMS, e107, and a couple of others, and they all seemed to make my job a lot more difficult (especially Drupal omg). If it wasn’t the CMS itself, it was the community under it. They were either lacking (or absent), or in some rare cases, complete jerks! Naturally, I didn’t want to spend sooo much time just trying to learn the bare minimum of the CMS when I’m more concerned about the product the site is supposed to promote.

So after that exploration, I went back to my own CMS. I managed to get a lot farther….faster than I expected. This was for my main site. While working on that, I needed a site up quickly for my Comics site and opened a WordPress.com account. I simply love it! I love the back end, I love the cool article features that are there that help with my posting (scheduled post is the best!), and there is so much more I just love about the system.

So now here I am at WordPress.org and I’m wondering if WP will work for both of my sites. Here are some of the particular needs for both sites.

1. User Management System (with user rights, credentials, and possibly group system)
2. Style change on most current post on front page. After 30 days, style of post changes to default (front page only)
3. Some kind of event planning system

The other thing though is that each site has 1 specialty application which from my reading I hear WP isn’t really good for. To refine what I meen, the first site has a Client management system that allows clients to post feedback, upload content where I can see and edit in the administrative backend, and the user has the ability to rate and post feedback about their service. The other site has it’s own management system for comics that ping specific information about the user logged in such as account information, credits available, etc.

Finally my questions (srry)
What I can do is have both these applications separate from WP using it’s own Admin, but my question is would it be possible to add some kind of link or option in the Word Press backend to those separate backends? Is it advisable? If the alternative is make a plugin, is there a huge learning curve to learn how to do this? What about handeling sessions and users if I were to link out to my seperate admin. Is it difficult (or possible) to recall the user in my application?

I’m pretty sure I have more questions regarding this issue. Any help would be appreciated. WP takes a huge load off the mundane tasks in the backend and if I can utilize it to fit my applications, I would love to do so.

Thanks everyone! If you’d like to see my current website, you can check it here:
http://www.keyjaycompound.com
and the site I set up using WordPress.com can be found at:
http://kjcc.keyjaycompound.com

Thanks everyone 😀