how to give certain posts priority when displaying (custom post types)

Hello,
A couple questions i hope you may be able to help out with.

1. I am trying to figure out a way i can have certain posts (or listings) automatically have a higher priority than others. For reference i am using a directory theme "Superlist" and am selling listings. For example, lets say we have 5 listing package types. (basic (free), bronze, silver, gold, platinum.) I would like to be able to have listings for those who sign up for say the platinum package appear above listings for those with the gold package, and whoever lists with the gold show above the silver, and so-on… (and be sure that all paid types show above the free packages by default)
2. Extending this a bit further, i am wondering how i could limit the number of images a user uploads based on the same packages above. (For example, Gold package has a limit of 10 images, Bronze with a limit of 5 images, etc.)

Note: I have a development version of the site at equinerising.ORG that is basically a clone of the actual site. We can play with the code here with no issues. I will open access through the admin panel so you can have a look. Please advise.

Thank you!
Scott