"Migrating from DO/AWS/Linode isn't fun and productive." Huh? You can run more or less the same type of services on Azure that you can on AWS. I wouldn't even consider DO due to lack of load balancers and file backup services.
AWS and Azure are great, but when things get complicated, it means having good resources to help is critical.
note - from what I know, most early stage YC companies just use Heroku to solve many of these problems anyway.
Been playing with CoreOS though...
- Azure Cloud Services (PaaS)
- Azure Websites (PaaS light)
Unfortunately, when I last looked at it two months ago, both of them were quite unattractive, at least for Python hosting.
First of all, they have no support for automatically installing python dependencies, i.e. no support for pip. If you want to install e.g. django-rest-framework, you have to install it locally and then manually copy the installed files to Azure (with FTP, if I remember correctly).
Secondly, they both run Python on a Windows Server running behind the IIS web server. Besides the fact that you will walk along the road less travelled (Django is overwhelmingly deployed on Linux), there is a very concrete limitation: if you want to install binary packages (e.g. PIL or Pillow), you have to manually compile them for Windows (and of course copy them manually to your Azure server). Yuck.
If you want to use Azure, go with their IaaS offering (Azure Virtual Machines) and stay away from their PaaS offerings.
If you're just running instances then maybe it's not too much work - though you're still going to have to think about backup / restore, access control, autoscaling (maybe), cost tracking / allocation, etc...
I'm sure Microsoft are banking on a profitable percentage of YC companies becoming so wedded to that Azure systems that the opportunity cost of switching to AWS is too high.
Edit: Typo
You can spin up your own load balancer pretty easily. DO offers backup too.
In terms of bang for the buck, you can't really beat DO, unless you're giving your services away for free ...
If you treat DO as just another VPS provider and pay on a monthly basis does it offer advantages over the competition?
http://venturebeat.com/2014/01/02/digitalocean-fixes-securit...
In short, unless you have inside information, there is not enough information to determine which company is more competent or more trustworthy - it's not possible to judge which company you should trust with your business based on the available facts in an objective way currently, as the available data is easily attributable to simple bad luck.
In contrast, the performance difference is objectively measurable: http://joshtronic.com/2014/06/22/ten-dollar-showdown-linode-...
Regardless, I don't see how you can judge someone who's had at least two breaches more competent than someone who had zero. In all probability, DO didn't have any breaches precisely because they are more competent.