Bear in mind this is all my own kit, not owned by a large company or anything, so I don't have servers etc.
I have windows 7 Ultimate 64, running Outlook 2010, with two separate hotmail email accounts connected to it.

I have one of those hotmail email accounts connected to my ipad & iphone. All fine.

The problem is the calendar mainly - I want one calendar that syncs automatically across all 3 devices.
( Fucking hell Jeff I am not a robot, Mon 11 Feb 2013, 10:07, 2 replies, latest was 12 years ago)

I don't think you can simultaneously sync a hotmail calendar and an outlook one to Apple things
it needs one default calendar.

I've not tried very hard though. Also, don't use hotmail.
( the mighty badger Aphrodite, on a bar stool, by your side, Mon 11 Feb 2013, 10:09, Reply)

Cool, it's not far off the setup I have for my personal stuff.
ipad/iphone: That should sync Mail, Contacts, Calendars and Reminders via a standard 'Hotmail' style account. When you update on one, it should update on the other.... make it "Mail days to sync" as long as you can. I think it's "push" style, so at most it shouldn't take a minute to update the other one. Also the "Pull down to refresh" thing should force it to get the latest version.

Outlook 2010 for Windows: It's something I've not used in yonks'n'yonks, but apparnetly this should sort your out: office.microsoft.com/en-gb/outlook-help/use-a-windows-live-hotmail-account-in-outlook-HA010354935.aspx

Also, rather than use outlook as an app, have you tried www.outlook.com ? The interface is far slicker, nicer to use, and it'll be setup properly.
( G/PP 💩💩💩💩💩&#128, Mon 11 Feb 2013, 10:15, Reply)

I've had a look at outlook.com
Didn't like it.
( Fucking hell Jeff I am not a robot, Mon 11 Feb 2013, 10:21, Reply)