Lets say I have $1000.00, and I want to set up a dating site from ZERO, am I going to be able to get the software, hosting, domain name and all that is needed to have the site up and running, will I be able to win some money like this?
To set up your own real site you would most likely want to get your own server. The more money you spend on one the more traffic it would be able to handle. I don't think $1,000 will get you very far making a profitable site and being able to maintain it.
probably not unless you have friends who can write very good code.
Things like dating sites require a lot and even a basic website for a normal person if they cant write code can cost $300+.