It would definitely be quicker if you could get someone like that on board right away. It's just not a given that that's possible. Depends on how compelling your idea is, etc.

But if you're already familiar with the trio, that's all you need to get started. Try to go ahead and build your prototype with Express.js, a Node.js web framework.

Server-side/backend:

http://expressjs.com/

http://nodejs.org/

Client-side/browser/frontend frameworks:

http://twitter.github.com/bootstrap/

http://ajkochanowicz.github.com/Kickstrap/

http://html5boilerplate.com/

Tutorials for HTML5 Rich Web Apps:

http://www.html5rocks.com/en/

I am planning to spend the next month or so getting up to speed on the following:

JavaScript + NodeJS (Given how widely supported and used it is)

Twitter Bootstrap (Really easy to build front end)

I have considered Ruby/Python however think that the learning curve is too great at the moment. I just want to know enough to build a good looking site that has basic functionality.

HTML5 is attractive but will have to wait for now.

> Try to go ahead and build your prototype with Express.js, a Node.js web framework.

Good recommendation: node+express rock