Any good posts to refer to? About pictures or text boxes fit into columns, typearea and margin.

@dublove

Not a problem - with a right tool. 

With normal scripting - you would've to react to an event - not sure which one as there is no "resize" event for objects so maybe onClick() or something like that - and add eventListener to each object... 

Or with a right tool - like my ID-Tasker (not free) - you could work in "Interactive Mode", where IDT actively monitors selection and can react to what has been selected, how many items has been selected AND in what order - so there can be a different reaction if you select Rectangle+TextFrame or TextFrame+Rectangle - plus a lot more conditions. 

In your case, IDT would save proportions for each object - either in bulk or you would've to select object and then resize it - then check if you've changed width or height and then change the other one. In case you change both - you would've to set which one has a priority - height or width. 

I don't remember, but I think IDT could even do it "live" - but I've to double check. 

It seems to me that everything after dragging a placement rectangle into a desired location, using snaps to margins and guidelines, then requires some degree of judgment to size and scale a photo or other image. Automated adjustments would have to assume a given image proportion and fixed cropping/scaling, if any. Useful for repetitive placement from standardized image (sizes), but perhaps more of an area where designer control is going to be required.