Hi Milburga6,
Thanks for coming to Apple Support Communities for help today! It sounds like your Mac Mail isn't working correctly and the iMac has to be signed into iCloud every time you restart.
You may find this page helpful: If you can’t send or receive email on your Mac.
This article has steps that can help explain why the Mail app isn't sending or receiving email on your Mac: Use Mail Connection Doctor.
For the iCloud sign in issue, is the iMac a trusted device using two-factor authentication? Please see this article: Two-factor authentication for Apple ID.
If two-factor is enabled, signing into iCloud multiple times shouldn't be required.
I hope these articles have helped.