Misko Hevery (author of AngularJS) wrote a good blog post about how if you pair with a new hire for a day, you can bring them up to speed almost instantly. I tried it and it works - my new hires were committing real fixes by the end of day one.
An additional benefit is that the experienced and more senior developer will also have to endure the pain of setting up, and the undocumented parts, and may even fix them.
However, if I was looking for a technical fix, I think using Vagrant is far better than anything cloudy. The cloud is a tradeoff - you get the benefits of virtualization, if you accept the downsides of it being all remote. The OP's solution doesn't even allow you to choose your editor! Vagrant gives you all the upside and none of the downside.
I love your linked article because it addresses the intangibles of imparting the mental model of the code. Many times this is the delay when a new developer comes into an existing code base. While scripts and cloud tools can reduce or eliminate the configuration overhead, the programmer still needs to understand what the actual code is doing.
The last company I worked for had this problem initially. There were multiple layers of software that needed to be built and configured just so. If there was a problem with your build, it would take an hour to get and build everything from scratch if things went without a hitch. They often didn't.
This changed once we started using a build server and automated builds. This made a complete build script necessary. The benefit was that script could be used to both spin up a new dev environment (except for installing IDE and local database servers), and syncing the dev machine. Every morning I would run this script and let it chug along while I went to my standup and/or read my morning email.
I think an automatic configuration script combined with the pair programming idea, even if the programmers are paired for a day, would greatly speed up the new dev up the learning curve and allow them to be productive faster.
http://misko.hevery.com/2009/06/12/what-pair-programing-is-n...
An additional benefit is that the experienced and more senior developer will also have to endure the pain of setting up, and the undocumented parts, and may even fix them.
However, if I was looking for a technical fix, I think using Vagrant is far better than anything cloudy. The cloud is a tradeoff - you get the benefits of virtualization, if you accept the downsides of it being all remote. The OP's solution doesn't even allow you to choose your editor! Vagrant gives you all the upside and none of the downside.