Hi Beau,
1) The current Banners plugin (v2.4.0) already have an similar function; but only for banner plans in AP.
The functionality required additional plugin Multi-field/Geo filtering.
2) Yes, automatically crop the banner image to an banner box size.
Doesn't make any sense display at all if your banner large.
Banners not a listing photos; banner originally supposed to be made in advance by a known size; not true?
Your constructive criticism is welcome.