Seeking advice on ASP, Ruby on Rails and Flash video

Hi,

I’m a total n00b when it comes to server side apps and i barely know my HTML and Flash when it comes to making websites. However, I work for a flash video website for South Asians called www.desivision.tv
Its basically a ghetto form of MTV but for Indians and as you can see by going to the website it is very very ghetto looking, which i blame on the previous web designer who has quit. Seriously, why the hell would anyone want their site to look like a ■■■■ browser.
Again, I want to stress that I have absolutely no knowledge of server side apps or coding. My boss’ website runs on ASP and I seriously want to retool it to provide a much simpler and easier look. I very much like http://youtube.com/ since it is similar to our website in many ways.
I’ve also heard of http://www.rubyonrails.com/ which is supposed to make it easier to publish content on your website, although I could not make heads or tails out of it.
So what I’m basically asking is

  1. how hard is it to make (designwise) a website like Youtube and make it easier for me to upload flash based content on it.
  2. Is that ruby on rails thing plain BS or is it worth taking note of?
  3. Am I talking out of my *** or will this require large amounts of money (i.e. hiring someone else.)
  4. If i were to hire someone, what would be their price range?

To me it sort of seems simple, which is why I even dare to ask, I mean just looking at Youtube it looks very much text based and somewhere in there is flash based content and that is it. I really like their simplicity, and I’m wondering if that is possible with ASP.

Thanks in advance.