Tuckman,
It's actually not really a dumb question at all.
A lot of times your first steps can be the hardest. It's really nice to have a forum like this through which you can get help and inspiration.
I'm not sure what kind of assets you have on hand (monetary, boxes etc.) so I'm gonna give you a couple starting points, and hopefully you can branch off from there.
1st off, if you have a spare computer or can sacrifice some speed off your CoH box, you should set up your own webserver.
There are tons of great applications out there through which you can do this, I would personally suggest going to http://www.php.net and learning as much as you can. PHP (originally personal home page, now "php hypertext protocall" or something exually as non defining) is designed to interface with Apache web servers and supports mySQL and simple MS Access databases for dynamic content. The great thing however about PHP and Apache is that it's all free and there is a HUGE open source community out there which designs programs, gives intuitive tutorials, and quality guidance for anyone seeking to design a PHP based web site/application.
If you want some suggestions for design mediums I can only give you the following suggestion: Try lots of demos. No two coders are the same and I'm sure webdesigners are equally diverse. Things I would start with are Macromedia Dreamweaver, Microsoft Front Page, and phpad (I have no idea where I found it - but I love it... it's quick, it's cheezy and it automatically translates RTF into HTML (it does a horrible job, but it's a start)). Oh and my personal favorite - notepad. I'm just really lazy and I can save it in any format I want.
I hope that gives you a quick idea of where to start, and with some more research and exploration I'm sure you can find a system that you like. Good luck with it mate. If you have more specific questions I'm sure you'll get more replies in the future.
Cheers-
RK