All those comments about using LAMP may be true, but when you're comfortable with Windows and not with Linux, stick with Windows. When the application you're going to run *can* run on Linux, then you may want to keep it that way, so you can move to Linux later on. When you're making money you could hire a Linux admin and then move. It may be cheaper in the end.
What is "the cloud" for you? I would think of Azure or Amazon EC2. I don't know of the fees that Azure has, but I believe Amazon has reasonable small servers (micro instances) that can be "scaled" (moved to larger instances) quite easily. At work we use Amazon, and I think it is great with the instant backup snapshots and all options that you have. But do you need it, and do you need it now?
My advice is this. Stay on your server at home, and use that as long as possible, unless you know that it's more expensive because of power and internet and license costs. In the mean time, start up an instance at Amazon. Configure it, get used to it. Run it, test your application on it. Set it up like another staging environment. Then shut it down, and start it up when you need to test more.
The most important thing about Amazon is that you need to set it up right. If you do it right, a big problem like Amazon had last month (4 days down) won't be a problem for you. If you mess up, it can mean disaster. So stick to what you know, and what works for you.
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