Images do not get "swapped" on hardware failure...they just restart (as is) on another node. If your familiar with virtualization, the VHD file just moves to run on another VM with 100% data intact.
I'd suggest Windows 20102 R2 (latest date) as it mirrors the Windows 8.1 kernel.
If you need high data reads/writes, make sure you set up multiple disk (limited to 1TB per disk) windows storage space array as described here:
You'll need to open up the ports 8086 externally (or SSL port) to connect.
There are many ways to get the files up so you don't need a VPN...GoodSync is good.
You control patching (and set the schedule) as it's your data (just like you do in the control panel with your Windows PC). Microsoft will not patch your servers in IaaS VM (only .Net PaaS code specifically written to run/scale in Azure). Many companies would flip out if Microsoft forced updates.
IaaS is also defined as Virtual Machines: