on my android phone and tablet, if I set up my hotmail account in the default Email app as an Exchange ActiveSync account, the Hotmail contact photos I have in outlook 2013 do appear on the phone and tablet. and I can edit those contacts, so that if I add
a picture to a contact on either device, it shows up in outlook 2013 on the next send/receive.
so, if you're keeping score at home, android can show me my outlook.com contact photos and let me add my own contact photos, but outlook.com and the windows 8 (and 8.1 Preview, if it matters) People app can't. or won't.
this also means that our outlook contact photos are already being synced to, and are already living in, the outlook.com cloud with our contacts, like we expect them to be. I guess Microsoft just isn't showing them to anyone who hasn't bought outlook.
or an android device.