let me give you few guide lines but note that his is custom development and it's beyond the scope of this support as you mentioned.
1. You will need to
- Amend FileGallery WebPart in order to have events necessary for you to choose the images
- setup FileGallery to display only wanted images (Note: there are many WebParts saving images to Upload folder so you need to specify what to choose by setting ParetnEntityId)
- edit Quick news post WebPart and add FileGallery in order to choose an image from uploads
2. You will need to choose from two approaches
- Amend News WebPart in order to support different tags
- user NVelocity (http://nvelocity.sourceforge.net/
) syntax to trim down the chars
Let us know if you need more information.