What DMG are you using for the 10.14.5 update? The one directly from Apple? If so, then that's at least part of your issue. The installer pkg is located inside that DMG when mounted, which is what you want to copy up to your Jamf server to deploy, not the DMG itself. It will never get installed if that's what you're pushing to clients.
@mm2270 Can you recommend a good way of getting or creating that .pkg I tried using your packager (great tool btw) and was not able to get a .app from it.

I would use composer but to my Knowledge I don't think I can just drag & drop the .dmg into the composer and save it as a .pkg and deploy it that way?
So there's no need to use any tool for this. Simply upload the .pkg located inside the mounted disk image, as is, to your Jamf Pro environment, whether you do that through Jamf Admin or directly in the web UI if you have a cloud distribution point. Either way, Jamf takes those packages as is without a need to repackage them or add them to some other package or what-have-you.
My App Packager tool is for taking an application bundle (ending in .app) and creating an installer package (.pkg) into it. That's why you can't use it with an existing .pkg. Wrong tool for the job. :)
Edit: That is, if I'm understanding your situation correctly. I'm taking it that you downloaded something like this from Apple? - https://support.apple.com/kb/DL2001?locale=en_US Or the Combo version of that hopefully. If so, just mount the disk image and find that installer inside it and use that.
Open (mount) .dmg.
Copy .pkg out to desktop.
Drag .pkg to Jamf Admin
Set policy to use the .pkg.
@Taylor.Armstrong of course it would be something this simple! lol
Does anyone know why it would not have pushed out the Smart group install via Actions --> Send Remote Commands --> Update OS version and built-in apps --> Download and install the update, and restart computers after installation.
This never did anything to my set test machine when completed, hence why I had to create the policy to force the install.
Also after creating the policy and it executes on the machine the computer goes into a boot loop and try's to install the the patch update over and over. I feel as this is may be due to the fact that I tied the policy to a Samrtgroup. These machines still show up as non patched till recon.