We had on-prem. We swapped to cloud.
Jamf now maintains the updates for us.

It gave us Cloud distribution too. This helps keep you secure if you use Self service at home for your users. The outside users connect to the cloud, the internal users connect to your existing distribution points. You dont have to open access to the internal servers for it to work.
We find the cloud to be worth it for us.

@jonros Here's some of things that make Jamf Cloud more appealing than on-prem to me:

• No install issues with JSS upgrades and backups. Jamf handles ensuring the upgraded instances come up properly, and if they don't they handle resolving the problem.
• A Jamf Pro Distribution Point that's fronted by the AWS CloudFront CDN. If you have a workforce that's dispersed geographically you'll get better performance than a DP hosted in your DMZ.
• Hosting in Jamf Cloud greatly simplifies the architecture of your Jamf Pro infrastructure when it comes to what servers you'll need in your DMZ, potentially eliminating all of them depending on what you're using to authenticate users.

What the others said, but for me not having an on-prem server to maintain (OS patching and Jamf application patching) was the big benefit so I could just do my work.  We require a rigorous OS patching routine, so moving to cloud opened up hours of available time each month, and freed me from the "keeping my fingers crossed that Tomcat will start after applying patches" freakout every month.

We still need to maintain a Jamf Infrastructure Manager (JIM) server for access to Active directory, but that was the case either way, and the JIM requires much less maintenance than the Jamf app.

Thanks for all input. :)