Numbers 1, 2 and 4 are very easy to satisfy. Several people have already posted lists of ideas that they and others maintain. I seem to recall Y-Combinator post

Numbers 1, 2 and 4 are very easy to satisfy. Several people have already posted lists of ideas that they and others maintain. I seem to recall Y-Combinator posting lists of the types of projects they wish to look at in the future too, so it would be worth searching for them. If you can't self host then .NET hosting is going to cost you around US$10 a month, although there are deals to be had - I think I pay $35 for 6 months of web and SQL Server hosting with a company that is passable for what I need it for. Unless you have a real passion to learn something new, I'd stick with the languages you now, it will be much quicker to get to where you need to go than if you learn a whole new language. But the problem is in monetization. Firstly if you can get an idea from start to making money in 6 months (for example) then I don't think there is really a cap on what you can make, I can't see a reason why $400 per month would be all you would want to make, and if you make something that can make money you should always be able to find new users (an exception to that might be if you made something very specific to only a few people and had an easy way to market it - eg something 100 HN users might like and no one else). But defining a web app that you can develop and easily make money is not easy. Most people's "idea lists" have lots of very interesting ideas, few of them I can ever imagine making a penny. My suggestion would be to look around you, you have a job, is any of the software you develop something you can clone and sell to other businesses (there are legal issues there, but you can often work around them and it depends where you are). Are there everyday tasks that people are using spreadsheets or Access DB's or paper to do that you could create a system for and charge $10 a month? Find an idea like that, spend 10, 20 or 50 dollars on Google Adwords pointing to a fake sales page and see if you have a market. Good luck.