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After updating a 9500 to 17.15.03 is pulling it into the meraki dashboard fairly straight forward?
Take a look at the documentation.
https://documentation.meraki.com/Cloud_Monitoring_for_Catalyst/Onboarding/Cloud_Monitoring_for_Catal...
Manage Cisco Catalyst in the (Meraki) Cloud
Provided your infrastructural networking is setup correctly (Eg. network configuration and firewall rules), it's generally a simple process.
The links @alemabrahao posted above has all of the required information in detail.
Support for the C9500 (device configuration mode) is only coming in 17.18.x I believe the documentation right now says it is not supported yet.