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 (Note – the file will begin downloading once you click the link):

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

To find updates for older versions of QuickBooks, including the R14 update, visit the Qtools website.