Hi Christina,
It seems like you need to print a map for each repeat, and for object 60 which includes 83 assets as you mentioned, it will need to print 83 maps. Therefore, the print job for object 60 exceeds the time limitation of 10 min for one object.
Here is the workaround for the issue, and you can print the object 60 separately using the method below:
1. In connect, create a new survey from the existing feature service - the related table containing the result of the repeat (83 assets are in this table)
2. Find this survey and go to the data page, only keep the section within the repeat in the report template
3. Use the filter to find all record for object 60, and print the report for them
In the meanwhile, I encourage you to contact Esri Support to raise an enhancement issue. Our Support team will assign an official case number for your records. This number can be used to search for and subscribe to the bug on the Esri Support site. If the issue is reported by other customers it will be attached to the same case report, which helps us assess the impact of the issue and prioritize it accordingly.
Thanks,
Ruth