Mac Outlook 2011 - moving folders from On My Computer to Exchange Server

I've just noticed a very odd peculiarity about using Mac Outlook 2011 with an Exchange server.

I am hoping to write a script that will allow me to highlight a folder On My Computer and move it onto the Exchange account. I would like to do this because I have a client who has very poor wrist strength and clicking-and-holding is very difficult for them.

So here is the strangeness described in three parts:

1. 
   

   From the Exchange server tree, right-clicking a folder and selecting "Move..." will bring up a search dialog box that will allow me to type the names of a folder I would like to move the data to. However, it will only search the Exchange server and will not find folders that reside On My Computer.

   
   


2. 
   

   The same goes for when right-clicking a folder from the On My Computer tree and selecting "Move..." - a dialog search box will come up that will only search folders in the On My Computer tree and will not find folders on the Exchange server/tree.

   
   


3. 
   

   Now here is where it is really strange. From the Exchange server account/tree, I can highlight a folder and from the toolbar click the "Move" button/drop-down menu (the icon is folder with an arrow on it) and select "Choose Folder..." which brings up a different search dialog box (as opposed to the one comes up from right-clicking) that does find folders located On My Computer. However, when I highlight a folder On My Computer the "Move" button on the toolbar becomes greyed out.

   
   

If anyone could suggest a starting point (like how to even envoke the mail folders search dialog box) or has any suggestions I would greatly appreciate it.