URL Structure Using Pages

I’m trying to create a simple yet organized url structure for my website, and am having a few issues on getting things exactly how I’d like them.

Here’s what I’m trying to do.

My site has categories such as Bars, Clubs, Restaurants, etc, and I want a url stucture like so:

sitename.com/
Main page

sitename.com/category/article-name
I found a plugin that removes the word “category” from the url, but I haven’t found one that replaces it with the category name. I’m ok with it simply being sitename.com/article-name, but the above is preferred.

(I’m going to substitute “category” with “bars” from now on.)

sitename.com/bars
This should go to all posts related to bars, be it a review, an event, etc, just like categories work now. The above plugin makes this url work by stripping category, and replacing it with the category name when actually selecting a category.

sitename.com/bars/listing OR sitename.com/listing/bars
I need to have a PAGE for each listing (Bars, Clubs, Restaurants, etc), as I’ll need to use a plugin to get a A-Z listing, or something along those lines. Either way, a post wont work, so this needs to be a page(s). The problem is, when you create a page, you can only edit the url to be sitename.com/whateveryouwant, but it can’t be sitename.com/something/whateveryouwant. I would like to have “something” be the category.

My primary concern is figuring out how to make a “listing” page for each category be at sitename.com/category OR sitename.com/category/listing, but the built in category system doesn’t seem to allow that, and the permalink changer in on the PAGE page doesn’t allow you to add a / to the url. If anyone knows of a plugin that would let me do a A-Z listing on all bars / clubs / restaurants on a single page, that would fix everything, otherwise I need answers to the above.

Thanks for any and all help 🙂