One of the issues I had seen after an upgrade to GP 10 was that "Send to PDF" with Outlook 2003 had stopped working. Microsoft Tech Support responded saying this was an identified issue which would be resolved in SP1. SP1 is due in November.
I saw somebody else facing this issue in the newsgroups, so decided to post the options I knew of here.
So here are your options in case you have upgraded and are facing this issue
1. Upgrade Office 2003 to Office 2007. This issue exists only with Office 2003. We ended up taking this approach!
2. Wait for SP1.
3. Use a work around to print a PDF and attach it manually.
Use the Print Setup Window to set Adobe PDF as the printera. Open the print setup window and change the printer name to “Adobe PDF”
b. Click print on any report, a PDF would be generated. You can save this wherever you want.
c. Attach the file manually to a new email.
When you Click Print a PDF would be generated. You can save and attach this to an email
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