migrating database-driven site to WP

I run an entertainment news site that is cobbled together with various dynamically-generated and static php pages.

I’ve toyed with the idea of moving to WP as a CMS so I can take advantage of its various features, but I’m wondering how I would migrate some of my site’s features.

1) we have historical coverage of events like the Oscars. One php file (say oscars.php) is able to grab written coverage and database info for each year…so if a person goes to /oscars/32nd/nominations they get the info for that year. How would that work in WP? is there a way of creating a page template in WP that would be called oscars and then depending on what came after it /32nd/winners, /32nd/nominations, it would display different info?

2) we have huge galleries of photos we’ve taken as part of awards night red carpets. I realize that there are gallery plugins for WP, but our galleries automatically search the names of the people captioned and link to their bios on the site if they exist. Again is that just a matter of creating a custom page called galleries and tossing our pre-existing php calls in?