Installing osx in Vagrant is probably possible, but it will probably be quite complicated, and in fact it is not like a tramp.
As for your other questions, the tramp sounds like a perfect fit.
With Vagrant, you can start Ubuntu vm and configure rail settings. Then you can simply forward the port to your local computer in vm and download the rails site as if it were running locally on your Windows PC. Fast google gets this stray box that looks like it can work for you - https://github.com/amaia/rails-starter-box
To work with the site, you can simply share the folder between vm and your local machine, which will allow you to edit images and code using your window applications (Photoshop, sublime), so you actually do not need to install them in ubuntu vm at all, and can pretty much work as usual.
Git is the same ... I prefer SSH to stray boxing and use git on the command line in ubuntu, but you can just as easily use gitbash or tortoisegit from windows in the repo folder. works just as well.
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