To get around the dreaded update error, you can download the file with the embedded update below:

From intuit.com:

We can install your QuickBooks 2009 with the r14 update. Here's the direct link installer for QuickBooks 2009:


http://dlm2.download.intuit.com/akdlm/SBD/QuickBooks/2009/R14/QuickBooksPro2009.exe



https://community.intuit.com/questions/1220631-how-can-i-get-update-r14p-for-quickbooks-2009