My dad's personal tech set-up is as follows: - Windows Desktop, running Windows 8.1 (he will not upgrade to 10 until he absolutely has to) - 64GB iPad Air 2 with Cellular running iOS 9.3 - Google/LG Nexus 5X running Android 6.0.1 His desktop has Office 2007 installed and he insists upon using Microsoft Outlook for E-mail/Contacts/Calendars. I gave him an Office 365 Home subscription that he has yet to activate (I assume he's waiting until he absolutely has to use it). The goal is to have it so that his contacts and calendars sync and update across devices automatically and without any manual and/or cabled syncing. Right now, he has iCloud for Windows installed and I think iCloud currently has the contacts and calendars that came from Outlook 2007. However, I have found nothing that will easily and natively load iCloud's contacts and calendars into an Android phone, let alone use them instead of the contacts stored in Gmail. Similarly, if he uses Gmail instead of iCloud (as the cloud-based contacts/calendars service of choice), the iPad will be fine using it instead of (or even in addition to) iCloud, but I have found no easy way to get Outlook to update its contacts and calendars database from Gmail that ISN'T a paid feature of Google Apps for Business. How would you guys solve this problem?