I'm looking fro something like an award system. Where I can assign multiple different (specific) images (small gifs) to a member that show up under their name on posts. Is this in any way possible with this system?

I see that vbulletin has a rank system that allows images to be assigned as ranks that double up on eachother which allows you to put more than one image under a users name. Hopefully you have that also =)

Also, The island with the Top Posters, can I change that to represent the top ranked members based on my specific ranking, not posts?

Thanks

you can assign the image as a custom title, it'll show under their name and above the post count title (currently that is)

you'd have to recraft the query in the island file, but so long as you know what you're doing, no problem.