Advice Needed

Basically, I've been programming 'basic' web designed sites for like 9 years. But, I haven't got myself into PHP, CGI, and ASP programming yet. Lately I've been having the idea/dream to start a local "Yahoo!" site in my hometown area of northeast Wisconsin. My site would include free classified service, free e-mail, free personals, business directory, etc. I know I have a lot of work ahead of me. I'm still really far behide in the database programming knowledge. How hard is this going to be for me to complete this dream of mine? I would really like to stick to my Windows XP because of programs I have that use Windows. I noticed that Linux hosting is a lot cheaper and whenever I look around on the web at scripts and source codes its always linking back to Linux. Can someone please tell me what they think I should start to do as far as hosting for Windows and programming ideas. THANK YOU VERY MUCH!

-Casey
Sorry for the dumb questions. I know that most of your guys are webmaster pros.

I would pick up a Linux hosting plan somewhere that has a script installer like Fantastico. Then you can install a CMS type program that will do everything you need. If you want to program something like what you are talking about it is going to take you a long time to get the necessary skills.