So it wasn't as hard to narrow down as I thought. It's not a specific plugin, but rather the total. I believe I've worked out a way anyone with 64 bit Platinum can reproduce this. Though I'll warn you this requires fiddling your registry and shouldn't be attempted unless you are fairly computer fluent.
First get this Zip with exports of my VST Inventory (zip also contains a screenshot of what this bug looks like and a copy of these instructions).
http://www.pontari.com/sonar/InsertSynthBug.zip How to reproduce using Sonar Platinum 64 bit.
First start Sonar and in Preferences under File->VST Settings set the Scan Options to Manual Scan
This way Sonar will use the registry you are going to import from my computer to reproduce the bug.
Start Window Regedit
Goto HKEY_CURRENT_USER\Software\Cakewalk Music Software\SONAR\Cakewalk VST X64\Inventory
Export that branch to a file on your computer (so you can restore your settings)
Delete the Inventory key
Now import the file "VSTInventory-BAD_1217 entries.reg"
This has 1217 VST Inventory entries (but I'm not sure how many actual plugins that maps too, which may be the real issue).
Start Sonar. Make a new project
Open the browser, go to the synth tab, click on the + sign to insert a synth. Your insert synth option should be grayed out. See included screenshot.
Exit Sonar.
Delete the Inventory Key and now import the other file included in the zip
"VSTInventory-GOOD_1216 entries.reg" it has exactly one less plugin
Restart Sonar and go to the insert synth tab. Notice the insert menu now works.
To restore your version of Sonar, exit, and once again delete the Inventory and reimport the version you exported at the start.