;tldr -> I'm running rails as part of a windows stack and it was less painful than you may imagine to setup.
I've been working on a little side project for a few years. I started the whole thing on the windows stack. I've got some c# console applications that extract transform and load data from various data sources and APIs on the internet. I've got an ASP.NET web application that exposes all of the data via a WCF DataService. The database is Microsoft SQL Server 2012. Since starting this project I've rewritten the full stack about 3 times (All in the .Net Stack). I have since learned Ruby, Rails, JS and the unix stack and want to leverage that knowledge.
The key to this project is mobile (iOS) and I was faced with these decisions: Phonegap or Native iOS Use my latest backend ETL (Extract Transform Load) tools to collect the data and consume the WCF OData webservice or rewrite the ETL tools AGAIN! and write a nice rails API to interact with via mobile.
Considerations: I've already spent a ton of time getting the C# ETL working. There is no (barely any) support for working with OData in iOS. The database is enormous (80GB) so I rather manage it myself, opposed to hosting it and getting charged per record. (May consider using heroku in the future) The database is MSSQL and the naming conventions I used do not follow the rails naming conventions.
A step in the direction towards deciding: I've done something that feels dirty... I installed rails on the Windows machine and I'm interacting with the MSSQL using https://github.com/rails-sqlserver/activerecord-sqlserver-adapter which is surprisingly good.
Things that have amazed me: Once database.yml is setup, (zero migrations) you can run rake db:migrate and it will populate the schema.rb file for you. (I've got to look into how this all works). So moments after getting rails setup I'm talking with the database sweet!
Once I had an auto generated schema I knew there must be a way to reverse engineer models from the schema, so after some digging I came across https://github.com/frenesim/schema_to_scaffold which generated scaffold commands that I was able to use to scaffold out all of the basic functionality.
So within hours I had a fully functional rails api, exposing data from my MSSQL database that is still being fed by my C# console ETL.
The most labor intensive part was manually building all of the associations between my 50 related models and manually overriding the rails conventions for table name with set_table_name and for all of the associations setting :primary_key, :foreign_key and :class_name.
I will probably go with Native primarily because I have some advanced UI stuff to do, but am still undecided at this point.