Hey there Herbert Spencer,
I understand that you are seeing some difficulty with your iTunes sync process, and that issues such as this can be really frustrating. I have a step I would like for you to take that may help you resolve this issue:
If some of your data syncs, but you see unexpected changes, you might need to reset your sync history. After you reset, you can replace all contact and calendar data on your computer or iOS device with the correct data.
To reset the sync history:
- Open iTunes.
- Hold down the Control and B keys on your keyboard to open the iTunes menu bar. Then, choose Edit > Preferences.
- Select the Devices tab.
- Click the Reset Sync History button.
If all of the data on your computer is correct:
- In iTunes, select your iOS device from the upper-left corner of iTunes, then click Info.
- Scroll down to Advanced. Under "Replace information on this iPhone/iPad/iPod touch," select Contacts or Calendars.
- Click Apply.
If all of the data on your iPhone, iPad, or iPod touch is correct:
- Remove the contact and calendar information from Outlook.
- In iTunes, select your iOS device from the upper-left corner of iTunes, then click Info.
- Scroll down to Advanced. Under "Replace information on this iPhone/iPad/iPod touch," make sure that Contacts and Calendars aren't selected.
- Click Apply.
If you can't sync contacts and calendars using iTunes for Windows - Apple Support
https://support.apple.com/en-us/HT203300
Let me know how it goes. Thanks for being a part of the Apple Support Communities!