Check-In

MDM has no predefined check in times, it relies on the 'push' mechanism of APNS. So check in is not needed, and cannot be forced. Switching networks sometimes helps to force an update if push fails.
User desktop picture (Background) is considered user's control by Apple, so you cannot manage that without Jamf Pro. (I remember you use Jamf Now)

HI @jared_f

Are you using this config profile for the desktop image?

What kind of "check-in" do you need? you could run a policy with a "Files and Processes" triggered at login. All you may need is "jamf log" in the Execute field
sudo jamf log from the help file:
log - Log the IP address, action, and username to the JSS

Thanks for the recommendations. I decided to go into out MDM settings and change the check-in to every ten minutes. I would like it to check for policies at login, but the support (for Meraki at least) is not there yet. Thanks for the recommendation though.