Hi Ohmann,
So what I think you are doing here is altering the state of the CMS interface form, in the subclass of the BaseHomePage page type from the cwp/cwp module.
You could use the "addFieldToTab" method for each photo and make sure the third argument is set to something like each Feature Title.
For example, the CWP module BaseHomePage has a DB field called "FeatureOneTitle" so you could place images above this by using:
$fields->addFieldToTab('Root.Features', UploadField::create('FeatureOneImage'), 'FeatureOneTitle');
'FeaturedOneTitle' is the form field you want to put your new field ABOVE. So this could also be 'FeatureOneContent' if you wanted this above the content block instead.
So what you are doing here is taking what is generated in BaseHomePage then altering it in HomePage before it gets displayed out in the CMS.
Hope that makes sense.