I started life as a programmer in 1981 on early Unix systems. I stayed a pure Unix person through 1995. Then 'stuff' happened, (business ownership), and Windows came into my life.
So in 2007 I start learning RoR, pure Windows. I deployed on Joyent, which is Solaris. I've successfully developed two large apps, developed on Windows, and deployed on Solaris/Apache/Mongrel, without major incident.
The only Windows issue I ever remember is that I had to force filesystem reads and writes into binary mode to fix a 'development' vs. 'deployment' issue.
I honestly don't see any problem with developing on Windows and Deploying on Unix. But I had an extensive Unix background, I'm not sure the story would have been the same had I not know Unix.
Also, I'll only ever work on the RoR apps I build for my business. I'll never need to build any other RoR apps, I'll never develop any plugins, never have to take over another project, never have anyone INSIST I include something only available in something that doesn't work well with my Windows development environment, etc...
I'd say this:
If you are responsible for developing a Web app for your employer, and that employer is Windows based, that SHOULD NOT preclude you from considering RoR as platform. The app would have to be deployed by a third party, unless your employer is large enough and the project important enough to warrant in house Unix systems.
So if you know SQUAT about Unix, you MAY need a little help along the way. If you go with a third party Rails host, check out their support forums, make sure there are people willing and able to talk a non-Unix person through any deployment/setup and maintenance issues.
I'll give you an example, on Joyent, if I want to run a migration, I have to go through their Database GUI thingy, log into the database, then 'execute' a command. OK, so I get a simple text_field where I enter input destined for a Unix shell, which is:
cd /user/myhome/sites/mysite && rake db:migrate RAILS_ENV=production
That might not have been so easy to figure out had I not had the Unix background.