Hello,
I cannot seem to manage any offline map areas across multiple maps. The save button is greyed out, no matter the settings. I have ensured sync settings are valid for all features, tested simple maps with only one feature (also sync enabled), created new maps from scratch, swapped basemaps, ensured no long fields within the maps. The maps themselves are offline enabled, and throw no errors when checking compatibility. Filed maps app also is failing to take an offline area periodically.
I know you said there are no errors when using the compatibility checker, but are you getting any specific errors messages either in Field Maps or when trying to generate offline areas in ArcGIS Online?
In the Field Maps app, go to troubleshooting and clear the logs, then try to download again. I'm assuming it will fail and might display some sort of short error, but most of the important info should be in the logs so go back and check. Since you cleared first, everything in the logs should be related to the recent error. If you can share that here, would be super helpful!