I would like to assign an existing drag/drop behavior to dynamically created items without having to rebind every time I generate a new element. 

Chrome 56 has a breaking change that impacts Kendo's drag and drop widget: https://developers.google.com/web/updates/2017/01/scrolling-intervention
The fix seems trivial - a CSS rule like "div[data-role=draggable] { touch-action: none; }".

The element should be draggable on screen.  Please refer the following Jquery draggable.
Kendo does not support such feature. 

https://jqueryui.com/draggable/

This will improve visual drag performance.

Fall back to existing (scripted) drag and drop implementation for browsers without native support.

See jqueryui.com/resizable/. Also checkout the nice set of options

I have a list view of unassigned users, I can drag and drop from listview into a treeview to assign them to a group node in the treeview. (This works) I need to drag multiple items to the same group node to add more than one person at a time.

multiple draggables to one dropTarget.

Columns are only able to be dragged and dropped to the limit of the grid as it's displayed on screen.  If a user wants to drag a column further, they have to drop it at the edge of the grid then scroll the grid across, then drag and drop it a second time to get it to their desired position. Can smarts be added so the grid scrolls left/right as a column is dragged beyond the a screen width's display of the grid?

Delay on draggable items.
When you have draggable items all around the site (not that much but many of them). 
If you try to scroll (on mobile devices) you may activate the draggable event of an item. So in these cases it would be useful if it waits some time (customizable) before it starts dragging the item.
Something like in jQueryUI: http://jqueryui.com/demos/draggable/#delay-start