@Philbeaux, State why you're considering changing to WordPress.
It appears there's no login use of this site, so no session management.
I can see how allowing comments related to various content might provide some usefulness + likely paid traffic will generate more income, since it appears part or all of your monetization relates to running Ad Units from Ad Networks.
When I take on a new hosting client, I always delve into their current site structure + determine if changes they have in mind, like changing to WordPress, really provides more benefit than problems.
Might be good for you to talk with smart people you know + ask for their advice. Be sure to pick people with long experience with online monetization + long experience working with WordPress.